Best New England Ski Resorts for Weekend Getaways

Best New England Ski Resorts for Weekend Getaways

New England ski resorts are open for 2018! For anyone looking to get away for a ski weekend in the Northeast from now until March or April, check out the resorts below. Each resort listed has great terrain, many accommodation options, villages offering you a break from your boots, and price points that won't break the bank, at least as far as ski weekends go.

Looking for more things to do in New England? Check out these posts about a Weekend in New Hampshire, Fall in Connecticut, and a Day Trip to Salem, MA!

Mount Snow

West Dover, Vermont * Opens for the season November 4, 2018

mount snow; ski; vermont

The Mountain

Mount Snow is the closest Green Mountain ski resort to both Boston (2.5 hours) and New York City (4 hours). It runs 20 lifts for its 600 acres of terrain, including the Bluebird Express that provides a front cover to cut the wind as you ride to the summit. The mountain provides mostly intermediate terrain, with a few steep diamond trails and a nice long, easy beginner trail down from the summit.

mount snow; ski; resort; new england; vermont; mountain


Two on-site accommodations are available at Mount Snow. The Grand Summit Resort Hotel provides ski-in ski-out privileges for the mountain. If you are looking for something more budget-friendly, stay at the Snow Lake Lodge across the street from the mountain, which is accessible by shuttle. Both locations offer hot tubs to enjoy during your après-ski time.

Village and Town

Mount Snow doesn't have a contained resort area, but it doesn't need one. The town of West Dover, Vermont, is a short drive away from the mountain and provides everything you would want in a ski town. If you want to be a part of mountain history, head for TC's Restaurant, home of Gold-Medal Olympian Snowboarder Kelly Clark. For something more upscale, sit in the dining room at West Dover Joe's. Looking for nightlife after dinner? The Snow Barn, a few feet from the mountain, provides drinks and live music most nights.

Overall Review: Given its location and size, Mount Snow is great for a short weekend ski trip or a long day of skiing if you're coming from New England or Eastern New York.


Killington, Vermont * Open NOW for the season! *

killington; ski resort; vermont; new england

The Mountain

Nicknamed "The Beast," Killington offers the biggest ski area in New England. Its size means there are enough trails to satisfy skiers of all levels. Thrilling black diamond trails challenge the best skiers, while beginners can stick to the numerous bunny trails or try a run from the summit entirely on beginner trails. Lift tickets are also some of the most expensive in the area at full price, but Killington often offers discount tickets if you spend time investigating.


The Killington Grand Resort Hotel at the base of the mountain is the perfect place to stay if you want all the comforts of a ski hotel. However, ski cabins are much more popular at Killington, as many of them have lift access, offering ski-on/ski-off capabilities. Killington's Managed Condos website or AirBNB can help you locate your ideal accommodation, whether it's a 12-person cabin with a private outdoor hot tub and indoor sauna, or a single-family two-bedroom bungalow.

Village and Town

Killington's Base Lodge offers numerous dining options for hungry skiers. Favorites include Preston's and Killington House of Pizza. If you want to venture into the cold for some nightlife, you must check out the Wobbly Barn, Killington's infamous music house and nightclub.

Overall Review: While Killington doesn't offer the on-site resort experience you may expect out West or in Europe, it has the best mountain in the area, so it's the best destination for serious skiers and their friends.

Jay Peak

Jay, Vermont * Opens for the season November 23, 2018 *

jay peak; snow; ski; resort; new england; vermont

The Mountain

Jay Peak offers 385 acres of terrain with 79 trails. However, it boasts the encouragement of off piste skiing as well, with 100+ acres of glade terrain. Advanced skiers looking to challenge themselves can take advantage of this additional acreage, while advanced-beginner skiers will find the intermediate trails accessible.


Jay Peak offers numerous accommodation options, all connected with their convenient shuttle service. For a hotel-like experience, stay at the Hotel Jay, Tram Haus Lodge, or Stateside Hotel. Many condos and cabins are available for larger groups who prefer their own private residence.


The New England ski resort with the most options available when you're ready to give the skis a break is Jay Peak. The Pump House indoor water park is a guest favorite with water slides, a lazy river, and indoor surfing. Access to the Pump House is included in your Ski and Stay ticket. The Ice Haus indoor ice skating rink lets you brush up on your other winter sport while you are on vacation. With 16 on-property restaurants, there is something to accommodate everyone's tastes at Jay Peak. At night, a few of the bars provide live music. If you want a quieter evening, see what's playing at the Movie Theater next to the Stateside Hotel.

jay peak; pump house; waterpark; indoor water park; vermont; ski resort

Inside the Pump House

Overall Review: A large mountain near the Canadian border, Jay Peak offers a full day of skiing and plenty of dining and entertainment options off the mountain to keep you occupied for a long vacation. 


Carrabassett Valley, Maine * Opens for the season November 19, 2018 *

sugarloaf; maine; mountain; new england; ski resort

The Mountain

Sugarloaf is one of the most popular mountains in Maine. Though somewhat difficult to reach, traveling on about 30 minutes of dark, local roads after you pass Portland, the journey is worth it. Sugarloaf Mountain offers 162 trails, which are evenly divided among beginner, intermediate, and expert options. The signature feature at Sugarloaf is its summit lift that is the only lift to bring skiers to trails above the treeline in the East.


Sugarloaf Mountain is in the middle of nowhere, so you're going to want to stay on the mountain. The Sugarloaf Mountain Hotel offers beautiful rooms at the base of the mountain. If you don't want to stay in a hotel, your other option are the ski-in/ski-out condos and cabins on the mountain.


Because of its remote location, Sugarloaf offers plenty to do on its property, and provides frequent shuttle buses to bring visitors to all its dining and entertainment options. The premium restaurant for a nice night out is 45 North. During the day, pick up a quick snack at Hunker Down or Alice & Lulu's between runs. If you're looking for a nice drink, The Widowmaker or Shipyard Brewhaus has got you covered. At night, take the shuttle to The Rack to grab a drink while listening to live music.

Overall Review: Sugarloaf's remote location mandates great customer service, a standard that the resort definitely lives up to. 

BONUS REVIEW: Mont Tremblant

Mont Tremblant, Quebec, Canada * Opens for the season November 22, 2018 *

mont tremblant; ski resort; canada; quebec

While this post is meant to focus on New England ski resorts, I would be remiss if I did not mention the absolutely best ski resort in the Northeast, just over the border in Canada. A 6-hour drive from Boston, or a quick flight from New York City, Mont Tremblant ski resort is absolutely worth the trip.

The Mountain

With 102 trails on four separate slopes, you could spend your entire trip covering new terrain with every run. The slopes are well-maintained with packed powder. Just remember to pack all your cold-weather ski gear: temperatures at the summit when I was there were below zero degrees Fahrenheit, without a wind chill!


There are cabins and condos available in the area of Mont Tremblant, but with such diverse options in the village, you should pick one of the official lodgings for your stay. The Fairmont and Le Westin provide the high-end, luxurious options. Homewood Suites and the Holiday Inn Express round out the hotel chain options with hotel suites including gas fireplaces and kitchens. For a more traditional experience, look into the Sommet des Neiges, Ermitage du Lac, and the Tour des Voyageurs.


When you arrive at Mont Tremblant's village, you will think you've been transported to a European ski village in the French or Swiss Alps, and not just because everyone speaks both English and French. The village was built in 1939, creating Canada's first ski resort area. As you walk through the lower and upper villages, you will pass many shops, restaurants, bistros, and bars. Make sure to stop into a shop for your traditional Canadian maple taffy, freshly made on Mont Tremblant's snow!

mont tremblant; canada; ski resort

Overall Review: If you want a proper European ski resort experience, take the time to visit Mont Tremblant. Also worth noting for American visitors, this luxury ski resort is a bargain due to our favorable exchange rate! It is also advised to take advantage of American bank holidays to visit this Canadian destination: many Montrealers venture to Mont Tremblant on the weekends, but it is virtually deserted during the week. I had an entire trail to myself on Martin Luther King Day a couple years ago!


Ready to plan your ski weekend? Find some of my favorite ski gear, like goggles, helmets, jackets, and base layers here!

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*Note: some of the links contained in this post are affiliate links. This means if you make a purchase through them I may receive some compensation, at no additional cost to you. As an Amazon Associate I earn from qualifying purchases.Thank you for supporting this page!


Best New England Ski Resorts for Weekend Getaways
Best New England Ski Resorts for Weekend Getaways
Day Trip from Boston: Salem

Day Trip from Boston: Salem

The city of Boston has a ton to offer, but if you want to get away for a day, there are exciting things to do in all directions: North, South, West, and even East!

Some of my favorite day-trip destinations from Boston are the Harbor Islands, the Cape, Patriot Place, Wrentham Outlets, Gloucester, and the Nashoba Valley Winery. If you have time, they are all worth checking out. However, I want to highlight a place I know well that is merely 30 minutes North of Boston: Salem, Mass.

Welcome to Witch City

Bewitched statue in the center of Salem

If you hop on the commuter train at North Station or drive up Route 1 for a half hour you may end up in historic Salem, home to the Salem Witch Trials of the 1600s. Salem embraces its history of witchcraft and has many witch-related stores on pedestrian-only Essex Street. It also offers year-round haunted or historical walking tours and invites visitors to see its Salem Witch Museum at any time of the year. If you really want to experience Salem in full swing, try spending a day or a weekend there in October. Throughout the month, the town brings in street performers and vendors, features carnival rides, hosts a parade on October 1 to kick off festivities, and lights off fireworks on Halloween. Almost all visitors dress up in costume, especially on Halloween, so this is the perfect time to dig out your favorite werewolf, vampire, or even witch costume!

You can even take a self-guided walking tour of locations seen in the 1993 film “Hocus Pocus”: here we are in front of the Ropes Mansion!

If Halloween isn’t your favorite holiday there is still plenty of non-witch-related fun to be had in Salem (though I would strongly recommend going sometime other than October in that case). Also on Essex Street you will find the Peabody Essex Museum, with many fascinating exhibits such as a giant statue of “The Thinker” by Rodin, on loan from Paris’ Museé Rodin. On the third Thursday night of each month the museum sponsors a PEM PM night, complete with a theme (such as Dominican Republican culture or anime and comics), musicians, dancers, food, drink, games and activities, and a chance to explore the museum.  Down by the water you can visit the House of Seven Gables, the actual house that inspired the novel of the same name by Nathaniel Hawthorne. If you prefer to just enjoy the food and drink scene in Salem, check out Far From the Tree Cider Tasting Room or the Sea Level Oyster bar with a rooftop deck overlooking the water.


Entrance to the Peabody Essex Museum

Large Rodin “The Thinker” Statue

PEM/PM Dominican dancers!

House of Seven Gables

Regardless of what you’re looking for, Salem is a great town to visit for a day or two near Boston!

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Year-round activities in Salem, Massachusetts

One-Day Boston Itinerary

One-Day Boston Itinerary

If you only have one day and want to truly experience everything Boston has to offer (or as much as you can in one day), here is a suggested itinerary.

8:00 AM: Breakfast

Start your day at Tatte (1003 Beacon Street, Brookline, MA: Green Line, C Line, St. Mary’s Street Stop), which is just over the city line in Brookline, MA. This European-style bakery has incredible pastries, lattes, and hot brunch options. In the summer months you can sit outside on the sidewalk to enjoy your breakfast, but thanks to a recent renovation there’s ample seating inside as well.

tatte; pastry; boston

Latte and Pastry at Tatte

9:00 AM: Tour of Fenway Park

Once you’ve finished your breakfast, walk over to Fenway Park for their 9 AM guided tour of the park. The website recommends arriving 15 minutes early for this one-hour behind the scenes look at America’s oldest ballpark.

10:30 AM: Museum of Fine Arts

Next, walk through the Fens to the Museum of Fine Arts (“MFA”), where you can wander around for a couple of hours viewing either the historical artifacts of Ancient Egypt and Greece, or the more recent artwork from Europe, Asia, and the Americas. If there is a special exhibit, be sure to check it out, they are always worthwhile.

12:30 PM: Lunch Downtown

Take the Green Line, E Line, from the Northeastern T Stop to the Copley T Stop and head to Atlantic Fish on Boylston Street for lunch. Again, if it’s a nice day outside, ask for a table on the sidewalk and watch the busy Bostonians hustle by. If you’re not a fan of seafood, then your destination is Stephanie’s on Newbury, which again has highly-recommended outdoor seating and one of the best brunches in Boston.

atlantic fish; restaurant; boston

2:00 PM: Boston Garden/Freedom Trail

Spend the afternoon after lunch walking the Freedom Trail. I know in another post I recommended starting the trail at the end, at the USS Constitution, and ending at the Boston Garden, but today you’ll start in the Boston Garden, which is only a 15-minute walk away from lunch. Spend time leisurely wandering Boston exploring the first half of the Freedom Trail, from the Boston Common to the North End, where you’ll end for dinner. If you read a guidebook or Google historical sites you can follow a self-guided tour, or you can join an official 90-minute Walk into History tour led by actors in historical costumes. If you choose the 90 minute tour you will also have time for relaxing by the harbor front or finishing the Trail with the Bunker Hill Monument and USS Constitution before dinner.

5:00 PM: Dinner North End

Enjoy a long Italian dinner in the North End, the Italian section of Boston. Pick any restaurant you’d like, you can’t go wrong with anything in the area, especially on the main drag Hanover Street, Salem Street, or any side streets off of these roads. My favorites include Ristorante Fiore, La Famiglia Giorgio’s, and Nico.

8:00 PM: Boston Symphony Orchestra or Boston Pops Show

From the North End you can either hop back on the T, the Green Line, E Line, at the Haymarket Station and take the train all the way to the Symphony stop, or just grab an Uber to Boston Symphony Hall. Depending on who is playing that night you can either watch a performance by the Boston Symphony Orchestra or the Boston Pops. Many world-famous musicians come to play with the BSO such as Yo Yo Ma, and if you are in town during the holiday season, you don’t want to miss the Boston Pops’ Holiday performance!

10:00 PM: Drinks at Top of the Hub

End your night with a couple of cocktails at the Prudential Center’s Top of the Hub restaurant while enjoying the spectacular views of the city. If your day in Boston is a Saturday, you can enjoy the live jazz music while enjoying your drink and the view.

boston; top of the hub

*Like what you see here? Contact me for your own customized travel itinerary!

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One-Day Itinerary for Boston, Massachusetts

Fitness in Boston

Fitness in Boston

There is no shortage of fitness options in this city! Boston is an epicenter of young professionals, and we certainly uphold the millennial stereotype of enjoying our studio classes and other workouts in the city.

Outdoor Options

Boston has many green spaces perfect for working out year-round. As the top running race in the world, the Boston Marathon, is held here, you will always see people who are either training for the Marathon or inspired by the runners running through the streets and on the Esplanade along the Charles River. If you are not at a level to participate in the Boston Marathon, the Boston Athletic Association offers 5K, 10K, and Half Marathon Races that run on the same streets through the city. In fact, the 5K occurs two days before the Marathon and the route has runners race right over the Marathon finish line after making the infamous right on Hereford, left on Boylston turns that marathon finishers make.

marathon; running; boston

Boston Marathon Top Runners

Biking has also become popular in Boston recently. Many people use the city’s well-constructed bike lanes to commute to and from work, but if you’re looking for more of a leisurely ride you can rent a Hubway bike with a credit card from any of the Hubway stands and then ride along the Esplanade or the Charles River Bike Path in Cambridge with no risk of interference from motor vehicles.

Many fitness centers offer free outdoor classes in the summer as well. Through these programs you can find yoga in the parks, early morning outdoor boot camp classes, and Zumba® by Healthworks at the Hatch Shell on the Esplanade in the evening!

Spin Studios

spin; cycle

What city full of young professionals would be complete without a plethora of spin studios? In Boston, you will find the national studios Soul Cycle, Turnstyle, and Flywheel, as well as local studios including B Spoke, The Handle Bar, and C-Town Cycle. Most of these locations offer free or discounted classes for first-time students, so you can try as many as you’d like without spending your entire vacation budget! My favorite – so far – is Turnstyle’s South End studio, but I have friends who prefer B Spoke, Soul Cycle, and Flywheel as well.

Yoga Classes

As with the spin studios, Boston’s residents would not be content without yoga studios around every corner. There are really too many to list, with local studios seemingly appearing every week, but some of my favorites include Down Under Yoga and Core Power Yoga (especially the C2 class). I’ve never had a bad experience at a Boston yoga studio, and similar to the spin studios, most studios will offer first-time student discounts or free classes so you can check them out while you’re in the city.

boston; yoga; fitness

Yoga in the shadow of Boston’s Faneuil Hall


Indoor Rock Climbing

A recent phenomenon in the Boston area is indoor rock climbing. Brooklyn Boulders and Rock Spot Climbing are the two favorites among Bostonians. Just show up with your sneakers and the gyms will have all the other equipment that you need, like helmets and ropes. A professional on site will be available to explain everything and help belay if you’ve never done rock-climbing before, so if you are up for something new this is certainly worth trying out!

Dancing Lessons

A common theme you will come to notice in my posts is that I love to dance, and try to fit dancing into my life as much as possible. Because of this, I must talk about dancing in Boston as a fitness option. In addition to just sweating it out in one of our clubs or lounges on a weekend night, Boston offers dance lessons at various studios for those looking to learn the basics of different styles of dance.

The Boston Ballet, the company that produces The Nutcracker each year, offers open adult classes to which you can drop-in. If you’ve never danced before, the company provides an Intro to Ballet Workshop where you can start your journey towards becoming a ballerina. If you travel a bit outside the city, The Studio in Brookline also offers drop-in adult dance classes for all levels in many styles of dance including ballet, tap, jazz, lyrical, contemporary, and pointe.

To learn some Latin dancing, especially Caribbean-style salsa, check out the lessons offered by Salsa y Control in Allston and Cambridge. The instructors from Salsa y Control also offer lessons at The Havana Club in Cambridge on Friday nights before the club is open to all levels for the best Latin dance party in Boston, where you can show off the moves you learned!

salsa; dance; boston

Night Out at the Havana Club


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Fitness Recommendations in Boston, Massachusetts

Top Boston Attractions

Top Boston Attractions

The other day a good friend asked for ideas of things to do in downtown Boston with his wife for their anniversary, and I completely blanked! To be fair, it was the middle of December and forecast to be the coldest day of the season so far with a high of 10 degrees Fahrenheit, so I was limited to activities that didn’t require being outside at all. Since that day, and in preparation for writing this entry, I’ve been thinking hard and talking with friends about what the top attractions are in Boston. I hope there’s something that appeals to everyone!

Go See a Game

red sox; yankees; boston; fenway; baseball

Red Sox – Yankees Game in the iconic Fenway Park

One of Boston’s many nicknames is the “City of Champions,” and with good reason: we have professional teams for all four of the major American sports (football, basketball, baseball, and hockey), and each has already won at least one national championship in the past 10 years. No matter which season you decide to visit Boston, you will be able to catch a game. If you want a relaxing, family-friendly atmosphere to both spend time with your friends and catch a game in America’s oldest ball field, check out the Red Sox at Fenway Park from April through September (or October if they make the playoffs!). If you want an intimate venue where you’re part of the action, head to TD Garden to watch either the Boston Bruins play hockey or the Boston Celtics in a basketball game: they share the venue, so be sure to check out which team is in town when you are in Boston. If you’re willing to make the trip – and pay the price for the tickets – you can catch a train or drive about 40 miles South of Boston to Foxboro to watch the five-time Super Bowl Champions the New England Patriots take on other football opponents on Thursdays, Sundays, or Mondays from August through January.


boston college; football; bostonFinally, if quintessential American sports are not your thing, you could always catch a New England Revolution game (soccer), watch thousands of top runners from around the world compete in the Boston Marathon, which takes place the third Monday of April every year, or cheer on crew teams in the Head of the Charles the third weekend of October. College sports teams in the area, including Boston College, Boston University, Northeastern, and Harvard, are also exciting to check out, and usually for a fraction of the price of their professional counterparts!

Check out Boston’s Museums

Boston is a world-class cultural center with many opportunities to see valuable works of art and experience scientific innovation at any of the museums around the city. I’ve listed some of my favorites with a brief description below.

Museum of Fine Art: Premier collection of world-renowned art from Ancient Egypt to modern America, including incredible temporary exhibits as well.

mfa; museum; art; boston

Isabella Stewart Gardner Museum: Site of the famous 1990 Rembrandt Heist, former mansion of Isabella Stewart Gardner filled with her personal collection of art she collected in her world travels during the 20th century.

Museum of Science: Contains not only typical science museum exhibits, but a great Planetarium and Omni experience theater. From March through November you can also head to the Observatory on Friday nights to check out the real night sky.

John F. Kennedy Library: The 35th American President was born in the Boston suburb of Brookline, where his house is still available for tours in the Spring and Summer months. His Presidential library sits on the South Shore of the city, accessible by public transit, and takes visitors through his youth, time serving in World War II, Presidential achievements, assassinations, and other contributions to the country by his family members.

New England Aquarium: While not technically a museum, this aquarium is great for aquatics-lovers to stop by with its multi-floor eco-system in the center, a touching-tank with sea rays and sharks, and the main attraction, penguins!

Mapararium: Take a tour inside this three-story glass globe built in the early 1900s, to see not only this impressive feat of architecture but also how the world has changed in the past century.

Many of Boston’s museums offer special monthly events as well with drinks, music, and programs geared towards adults, including the Museum of Fine Arts’ First Fridays, the Gardner Museum’s Third Thursdays, and Boston “Grown-Ups” Museum night at the Boston Children’s Museum.

Walk the Freedom Trail

Whenever I have family members visit me in Boston for the first time, they always ask about walking the Freedom Trail. While the trail is claimed to start in the Boston Common and end at the USS Constitution ship in Charleston, I would recommend going backwards and ending at the Common where there are plenty of locations to grab food or drink and relax when you have finished, including the original Cheers bar. There are 16 official stops on the Freedom Trail, which can all be found by following the Red Brick Line in the sidewalk (similar to Dorothy’s Yellow Brick Road in the Wizard of Oz). Here are the stops I find most interesting:

USS Constitution: From the late 1700s, this is the oldest commissioned warship still afloat. After surviving the War of 1812 fighting against the British troops, she was given the nickname “Old Ironsides.” You can buy tickets to go on board and take a tour while she is docked.

Bunker Hill Monument: The second stop on the trail going backwards, the monument has 294 steps to climb to the top for a unique view of Boston.

Old North Church: The oldest church still operating in Boston, the steeple of this church is where the lanterns were purported to have been hung, “one if by land, two if by sea,” to signal to Paul Revere how the British were approaching so he could set off on his midnight ride to alert the colonists.

Paul Revere House: Built in 1680 and purchased by Paul Revere in 1770, you can visit the house where Revere and his family lived during the Revolutionary War.

Faneuil Hall: Filled with cute shops and vendors on the first floor, the meeting room on the second floor is where our Revolutionary Leaders met during the war, and where the Sons of Liberty expressed dissent against Royal oppression. While here, you can also stop by the shops and eateries of Quincy Market.

Site of the Boston Massacre: Identified by just a plaque, you can stand on the exact spot where the British troops shot at the colonists to ignite the beginning of the American Revolutionary War. A reenactment to commemorate the event takes place every year on the site.

Old State House: Visit the Old State House for a fascinating museum about the Revolutionary War, then step outside to look at the golden lion statue sitting atop the roof: in 2014 a time capsule from 1901 with its contents in almost perfect condition was found in the lion’s head when it was taken down for restoration.

Granary Burying Ground: An incredible cemetery in the heart of Boston near the Common, including a giant monument with the name “Franklin” on it, under which Ben Franklin’s parents are buried. Other individuals of note buried in this cemetery include Sam Adams and John Hancock.

Massachusetts State House: Impossible to miss with its gilded dome, the Massachusetts State House was built in 1798 and is still used by State Senators, Representatives, and the Governor to conduct state politics. You can take a tour or just step in to look at the interior of the dome and artifacts around the rotunda.

state house; boston; history

Boston Common/Boston Gardens: The Freedom Trail begins, and in this case ends, at the Boston Common. Used for many public purposes, including witch hangings in the 1700s, today you can find many families and college students enjoying the sun in the Common in the warm months, and ice skating on Frog Pond in the cold months. Walk through the Common to the Boston Garden, where the Swan Boats continue to make their way around the Pond in the summer months after almost 150 years of operation.

swan boats; boston

Swan Boats in the Boston Garden Pond

Take in a Show

Seeing as it is currently the holiday season in Boston, I cannot imagine being in this city without catching one of the many shows available. Check out the schedule at the Boston Symphony to see whether the Boston Symphony Orchestra or Boston Pops are performing: if you are under 40 years old, you can get $20 tickets for select performances, and if you plan your trip to see the Boston Pops right, you could see John Williams himself conducting some of his hits from movie scores including Jaws, Jurassic Park, Star Wars, and Harry Potter! Many college music groups also provide cheap or free shows, including most Berklee organizations and the Boston College Symphonic Band, who performs at the Hatch Shell each summer.

If theatre is more your thing, you can check out Shakespeare in the Common during the summer months, or a hilarious version of Shakespeare with a drunk cast member not quite following the script in Sh*tfaced Shakespeare. Again, many colleges will also put on their own theatrical productions throughout the year.

You may instead choose to see the Boston Ballet (their version of the Nutcracker is amazing), a Broadway in Boston show, or check out a comedy performance at the Improv Asylum. Many top-billing performers also come through the city frequently, performing not only at big venues like TD Garden but also more intimate music venues like the Royale, House of Blues, and Paradise Rock Club.

Chromeo; boston; house of blues

Chromeo performing at the House of Blues

Of course, as in any city, you could also fill your days wandering the streets of Back Bay, Downtown, South Boston, and the North End, going on college visits to view the campuses of Harvard, MIT, Tufts, and Boston College, and sit by the water in the Seaport or at the beach, but I wanted to provide examples of some of the unique cultural experiences Boston also has to offer.

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Top Boston Attractions

Boston Restaurants and Nightlife

Boston Restaurants and Nightlife

Boston has a plethora of restaurants, bars, lounges, and places to dance and experience the nightlife! As this blog is meant to focus on high-end locales, I will highlight some of my favorite luxury restaurants, bars, and clubs. If you’d like additional information on any of the places discussed, or suggestions for less-high-end locations, please feel free to contact me!


  1. Eastern Standard

    The Eastern Standard provides your typical upscale American fare with a European ambiance. It is also just a couple of blocks from Fenway Park, making it a great place to go before or after a Red Sox game. They have amazing oysters sourced from the Southern Coast of Massachusetts due to their affiliation with their neighboring restaurant Island Creek Oysters (also highly recommended). This is also a hot spot for brunch with a fantastic Eggs Benedict and House Smoked Salmon. The rest of the menu, including the cocktail menu, rotates on a seasonal basis, but I’ve gone here for years and have never been disappointed. If you enjoy the hustle and bustle of the city, you can sit on Eastern Standard’s sidewalk patio in the heart of Kenmore Square in the warmer months, allowing you to enjoy the warm weather while engaging in some fantastic people-watching.

  1. Smith & Wollensky at the Castle

    Smith and Wollensky castle; steakhouse; bostonAt the end of the 19th Century, Massachusetts built a Victorian Armory for its First Corps of Cadets. It was one of many armories in Boston at the time, but is now the last standing Victorian Armory in Boston and  home to Smith and Wollensky , one of Boston’s premier steakhouses. When you arrive at The Castle, as the Armory is now called, you are greeted by the friendliest, most helpful staff, who bring you to your table in one of the many available rooms. There is certainly an air of elegance throughout the entire restaurant, though it is coupled with well-placed armory memorabilia. On top of the atmosphere, the food is incredible: the steaks, especially the filet mignon, are carefully selected and cooked perfectly. One of my favorite side dishes is the Truffled Macaroni & Cheese: if you can’t make it to Smith & Wollensky in the near future, their Macaroni & Cheese recipe is available online (I made this for my family one year for Easter and it was a big hit)!

    (Update June 23, 2018: Smith and Wollensky recently announced they will be closing their Castle location in Boston: locations are still open downtown on Atlantic Wharf and a new location is coming soon to Wellesley, MA)

  1. Babbo

    Babbo is an up-and-coming Italian restaurant in Boston’s up-and-coming Seaport district. A Mario Batali restaurant, Babbo brings a modern feel to classic Italian dishes. Last time I was there I ordered the Polpette Alla Griglia (Octopus on the Grill) and also tried the traditional Pizza Margherita. The octopus was a little spicier than I had expected, but still enjoyable and well-cooked. The pizza was relatively authentic compared to what I’ve eaten in Northern Italy, with a slightly thicker crust than the original Pizza Napoli. I also ordered the Sardinian Iced Tea, a mixture of prosecco, lime juice, and meletti amaro (an Italian liqueur), and it did not disappoint. For the wine drinkers, Babbo has an extensive list of Italian wines, all of which are fantastic. If you’re looking for something fresh yet classy in Boston’s hottest new district, Babbo is the way to go. One word of caution: as the Seaport is still being developed, parking can be a bit of a challenge, so if you are able to take the T instead, you can get off at Courthouse on the Silver Line, the closest stop, or take the Red Line to South Station and walk just over the water to Babbo.

Runner-Up Restaurants: Pier 6, Ristorante Fiore, Ruth Chris


  1. Top of the Hub

    No post about Boston’s food and drink scene would be complete without discussing the Top of the Hub, Boston’s sky-high, 360 degree-view restaurant and bar on the 52nd floor of the Prudential Center. Many Bostonians have mixed feelings about the Top of the Hub, and I’ve heard it’s meals are overpriced for mediocre food (I have never come for an entire lunch or dinner). However, its drinks are amazing – both the classics and specialty house cocktails – as well as its desserts. During the day you can enjoy your drink with one of the best views of the city in a very relaxed atmosphere, high above the aforementioned hustle and bustle. In the evening things get a bit more lively: one of my favorite things to do on a Saturday night is to sit in the lounge at the Top of the Hub, enjoying the live jazz music and watching couples try to showcase their skills on the dance floor.

    top of the hub; martini; boston

    Here I am at the Top of the Hub enjoying a chocolate lava cake birthday dessert and a caramel apple martini while looking out on Boston

  1. RumBa

    Named for its extensive selection of rums from around the world, along with the Bostonian pronunciation of “bar” (hence Rum-Ba(r)), the InterContinental’s RumBa is one of my favorite cocktail bars in Boston. While my friends and I are easily the youngest people by decades when we go here, grabbing drinks at RumBa surrounded by accomplished business professionals makes us feel suave and sophisticated. This is a great place to come either after attending an event in downtown Boston or on a weekend afternoon in the summer when you can sit on the deck by the water. Their collection of liquors is extensive. I almost always order one of the rum cocktails with Mount Gay rum, which takes me back to my days on the beach in Barbados enjoying local rum punches.

  1. Legal Harborside

    Boston has a large selection of rooftop bars that open in April and remain open through the Fall. A few even opened for a couple days this past February when we had a week with temperatures in the 60s! Every year one of my friends and I obtain a list of all the rooftop bars in Boston and vow to get to each of them during the summer, and while every year we fail, Legal Harborside is one rooftop bar we have made it to multiple times. Not only does this place have killer sangria, but it also offers small plates including some pretty intense, delicious sushi. Sitting over the water in the Seaport, Legal Harborside has a retractable roof, high top tables with a city view, and large white lounge couches, if you can snag one. This is also one of the hottest after-work and weekend places to gather, and if you don’t arrive early enough you’ll encounter a fairly long line waiting to go upstairs to the third-floor roof deck.

Runners-Up Lounges: City Bar at The Lenox, Lolita, Audobon, The Charlesmark Lounge & Bar


  1. Icon/Venu/Cure




    cure lounge; lounge; bostonSpace Entertainment throws some amazing dance parties at their clubs. The current lineup includes Cure on Thursdays, Venu on Fridays, Icon on Saturdays, and Cure again on Sundays. Cure is located under the Wilbur Theater – no, those people in line are not waiting to see a show, as I thought when I first went here – and has the most lounge-like feel of the three venues. It has many couches set up around and throughout the dance floor, though there is still plenty of space for dancing. However, don’t plan on using the couches unless you buy a table or make friends with someone who bought a table. Venu has a larger dance floor space in the middle of the club but much less personality than Cure: it is clearly meant for dancing. Icon (formerly Rumor) has two rooms with dance floors that include stages and VIP sections. Icon’s back room hosts Latin Nights on Saturday nights, but to control the crowds you need to either buy a table in the Latin Room or obtain a wristband from one of the club’s promoters. Because these are the only ways to access Icon’s Latin Room, the tables sell out quickly and it is very difficult to get a promoter to give up a coveted wrist band, let alone multiple wristbands for your crew. The difficulty with getting into the Latin Room is one of the reasons I prefer Cure Thursdays: Cure also boasts a back Latin Room, but movement between the main room and the Latin Room is fluid as long as there is space, no wristbands or tables needed. Regardless, you can’t go wrong with any of these locations if you are looking to dance and rub shoulders with some of the who’s-who of Boston: visiting sports teams and big name sports stars have been known to make appearances at each of these clubs.

  1. Bell in Hand

    Bell in Hand is America’s oldest continuously operating tavern. It was where the Sons of Liberty, including Paul Revere and Sam Adams, gathered to plan the American Revolution in the 1700s, and the notorious Whitey Bulger met with his cronies in the 1970s. Today it is frequented by students and young professionals as a great place to grab a drink and dance to either the live cover bands on the first floor or top-40 music played by a DJ on the second floor. Entrance into the bar itself can include a wait that is well worth it, with another line awaiting you inside to reach the second floor. Both floors offer great nights of dancing depending on what you’re looking for: while the second floor has a more club-like atmosphere, don’t feel that you are missing out if you decide to forego the second line to enjoy the first floor’s band.

  1. Alibi

    You won’t find as many students at Alibi as the other clubs: this locale tends to attract successful young professionals in their late-20s and early-30s. Located in The Liberty hotel, you usually won’t have to wait in line as long to get in here as some other clubs, and cover and tables are a bit cheaper, though there is less of a designated dance space. Instead, people just dance with their friends throughout the bar. If you are going out with people for whom dancing is not their thing, one of the nice things about the Alibi is that while some of you are dancing in the lounge, others can enjoy The Liberty’s calmer drinking areas Clink and The Liberty Bar.

Runner-Up Nightclubs: Umbria Prime, Scholars, The Brahmin

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The Best Restaurants and Places for Nightlife in Boston

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