Best Fall Activities in Central Connecticut

Best Fall Activities in Central Connecticut

For many people, Fall is one of the best times to visit and explore New England. Many people head north to Vermont or New Hampshire for leaf-peeping. If you are looking for something off-the-beaten-path this year, check out these great activities in Central Connecticut!

Looking for more Fall New England activities? Check out this post about a Fall Weekend in New Hampshire, and this one about what to do in Salem, Massachusetts!

Apple and Pumpkin Picking

Apple and pumpkin picking are two can’t-miss activities in central Connecticut. The season for apples begins around the end of August and continues through the beginning of October. Pumpkin season runs from the end of September through October. Check out either of the orchards below for your farm-fresh apple and pumpkin needs.

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Lyman Orchards

Many people visit Lyman Orchards every year for its apples and pumpkins, as well as it’s annual corn maze. Many other people visit just to purchase one of their well-known pies. If you have trouble deciding, go for the Hi-Top Apple Pie, which is perfect when served at Thanksgiving dinner.

32 Reeds Gap Road, Middlefield, CT 06455

Dondero Orchards

Growing up in central Connecticut, Dondero Orchards offered a no-frills fall experience for cheap apple and pumpkin picking. Over the years, its popularity has allowed it to grow into one of the most popular farms in the area. Pumpkins are no longer 10 cents per pound, but instead there are craft fairs, a farmers market, farm stand, and farm-to-table dinners offered by the orchard.

529 Woodland Street, South Glastonbury, CT 06073

Apple Festivals

What do Nutmeggers do after they’ve picked all their apples? We host apple festivals, of course! The two most popular festivals are held annually in Southington and Glastonbury.

Southington Apple Harvest Festival

Grab a fresh apple fritter and listen to the live music provided by the Southington Apple Harvest Festival! Complete with carnival rides, a craft fair, a pie baking contest, fireworks, and a parade this festival embodies central Connecticut in the Fall. You can always expect to see great musical acts: this year’s entertainment was opened by Bowling for Soup! Held the last weekend of September and the first weekend of October, you’ll have to mark this one on your calendar for next year.

75 Main Street, Southington, CT 06489 * 2019 Dates: 9/27-9/29, 10/4-10/6 *

Glastonbury Apple Festival

The Connecticut River Valley Chamber of Commerce hosts its annual apple festival in Glastonbury every year. As stated on its website, “For the 5th year consecutive year, the Apple Harvest Festival will feature three stages of live music with 30 emerging artists, a full midway of amusement rides, over 100 vendors, 25 food trucks/purveyors, the extremely popular Harvest Pub, the Angry Orchard 5K Road Race and all things fall in New England.” This festival will take place next weekend, so if you want to get the full Fall experience in Connecticut, hop in your car and drive down to Glastonbury for a day!

300 Welles Street, Glastonbury, CT 06033 * 2018 Dates: 10/12-10/14 *

Town Fairs

If you prefer fairs that have less of a focus on apples and more on animals, add the following agricultural fairs to your calendar. Although they have both ended for 2018, they are worthwhile to make note of for Fall 2019!

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Durham Fair

The Durham Fair is considered Connecticut’s largest agricultural fair. For just four days, you can visit the fair to see prize-winning animals, enjoy fresh or fried fair food, ride the rides at Midway, and see performing acts like Melissa Etheridge and Scott Mccreery, the two 2018 headliners. If the famous Topsfield Fair in Massachusetts is not an option for you, check out the Durham Fair instead for a comparable experience.

24 Town House Road, Durham, CT 06422 * 2019 dates: 9/26-9/29 *

Haddam Neck Fair

For a smaller agricultural fair in central Connecticut, spend your Labor Day Weekend at the Haddam Neck Fair. Started by the Haddam Neck Grange in 1910, the fair now spans three days and welcome tens of thousands of guests. It no longer just shows off animals and vegetables, but instead provides carnival rides, a variety of food, Country Western entertainment, a legendary tractor pull, and a recently-added 5K road race. If you want to experience a typical Connecticut agricultural fair without the crowds attracted to Durham, the Haddam Neck Fair is perfect for you.

207 Middle Haddam Road, Middle Haddam, CT 06456 * 2019 dates: 8/30-9/2 *

Vineyards and Breweries

Chateau Le Gari

Connecticut has over 35 vineyards and wineries to explore: impressive for a state where little is known about its wine. One of my favorites is Chateau Le Gari. This vineyard was founded last year by the former Vice President of the CT Farm Wine Development Council, Gary Crump. The property is beautiful and the wines are flavorful, with most of the grapes grown right on the property.

One of the best parts about this vineyard is the presence of Gary himself. When you arrive for a tasting you may be greeted by the former-Cajun behind the tasting bar pouring his own wine and telling you stories from his career and life. If you are lucky, you may even get to try some of his local cooking. Every Sunday afternoon, Gary makes and serves pasta with bolognese to his guests! Gary’s knowledge of wine is astounding, so if you can catch him while you’re here for a conversation, be sure to do so.

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303 South Main Street, Marlborough, CT 06447

Priam Vineyards

Priam Vineyards is located less than five minutes from Chateau Le Gari. In fact, Priam was also founded by Gary Crump! Stop in for a quick tasting, or bring a picnic lunch to enjoy on the back patio with a bottle of local wine.

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11 Shailor Hill Road, Colchester, CT 06415 *

Fat Orange Cat Brewery

A few years ago, Mike Klucznik started brewing his own beer for personal consumption, as many Americans do. After winning a number of home brewing competitions, he decided to open his own brewery. Sheila Mullen had ample space on her property in rural Connecticut, so the two built a barn to host the brewing operations and a small bar. The pair still travels with their team to national craft beer competitions, but if you like beer and are in the area, you should travel to the Fat Orange Cat Brewery to try the beer for yourself!

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47 Tartia Road, East Hampton, CT 06424 *

Pumpkintown, U.S.A.

If you only do one Fall activity in central Connecticut, you must visit Pumpkintown, U.S.A. In 1990, Sandra Peszynski of Paul’s & Sandy’s Too farm store painted faces on a few pumpkins, added some clothes, and invited the local townspeople to take photos. She had no idea that 28 years later, Pumpkintown would be the top non-scary Halloween attraction in Connecticut! The town now has a Saloon, Bank, Post Office (to mail your Pumpkintown postcards), Firehouse with a firepole to slide down, tires for jumping, a hay bale maze, tractor rides, and so much more! Don’t forget to take pictures!

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pumpkintown, pumpkin, fall, connecticut, central connecticut

93 East High Street, East Hampton, CT 06424 *

Old Airline Trail

Fall is the perfect season for hiking! While you won’t find many tall mountains in Connecticut, there are many beautiful trails to walk, run, or bike along. The Old Airline Trail stretches about 25 miles from East Hampton to Thompson. Built in 1873 to connect New York City and Boston, the tracks have long been covered by gravel to provide a recreational area to locals. Ample parking is available every few miles along the trail, and access is free.

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Trail head: 69 Smith Street, East Hampton, CT 06424

Lady Katherine Cruise

Central Connecticut is often referred to as the Connecticut River Valley due to the Connecticut River running through it. One of the best ways to experience the river is by taking a cruise. The Lady Katherine departs from Middletown and East Haddam, and offers Fall brunch and dinner cruises so you can enjoy the foliage on the water. If you are more of a Halloween person, check out the Halloween Murder Mystery Dinner Cruise!

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Multiple Locations

Where to Eat in Central Connecticut

When you’re ready to take a break from all of the activities and grab some food, check out the places below! Central Connecticut has many amazing restaurants, but the three described here are especially fun in the Fall.

Goats N Roses

Goats and Roses provides one of the most authentic farm-to-table experiences in New England. As you pull into the parking lot on the farm, you are greeted by a farmhouse, tavern, general store, and goat yard. Grab a table – outdoor seating only – and pick one of your favorite farm dishes to eat. I recommend the Teriyaki Chicken Salad or Figgy Piggy Sandwich. After your meal, you can explore the property where you are likely to encounter some of the resident animals, like the chickens, peacocks, and of course goats!

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dining, restaurant, farm to table, outdoor seating, goats n roses, central connecticut

86 East Hampton Road, Marlborough, CT 06447 *

Rose’s Berry Farm

Rose’s Berry Farm is open for Sunday breakfast from June through October. Despite its short season, it may be the best Sunday breakfast experience you have. Everything served at Rose’s is farm fresh and farm-to-table, right from the farm it overlooks. Sitting high above the rows of berries and apples, you can enjoy waffles, pancakes, and french toast topped with seasonal fruit. Savory dishes are also available, but even if you are usually a fan of savory breakfasts as I am, this is one time to go the sweet route for the berries!

295 Matson Hill Road, South Glastonbury, CT 06073 *

Where to Stay in Central Connecticut

Most accommodation options in central Connecticut consist of your typical chain hotels: Marriotts, Holiday Inns, Homewood Suites, etc. These are great choices if are only using your hotel as a place to sleep while you explore the area. However, if you want to try something a little more traditional Connecticut, check out the options below.

The Inn at Middletown

This property was built as a private residence in 1810, and subsequently acquired by the State of Connecticut to be used as an armory. In November 2003, the Town of Middletown opened the Inn as “an upscale full service boutique hotel.” If you are looking for charm and location within walking distance to many businesses and restaurants on Middletown’s Main Street, this is the place for you.

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70 Main Street, Middletown, CT 06457 * (Click here to book!)

Griswold Inn

Founded in 1776 during the American Revolution as a tavern and accommodation for shipbuilders who moved to town, the Griswold Inn has been in operation for more than 242 years. Its rich history follows that of America. You can experience what it was like to join fellow revolutionaries in the early years of the country in the tavern, or have a more upscale experience in the full dining room. The Griswold Inn also offers 33 unique bedrooms for rent: some have fireplaces, some provide a view of Main Street, and others overlook the water. If you want to step back in history on your visit to Connecticut, check out the Griswold Inn.

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36 Main Street, Essex, CT 06426 * (Click here to book!)

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One-Day Itinerary: Havana

One-Day Itinerary: Havana

As an American visiting Cuba on the “Support the Cuban People” visa, you should have a set itinerary before you go that includes interactions with locals and meals at local, privately-owned paladar restaurants. Use the following itinerary for one day of your trip: if you like what you see, contact me for a customized, full, multi-day itinerary!

7:00 AM: Breakfast

Begin your day early with breakfast at the Locos por Cuba restaurant. When you have finished eating, flag a taxi (or colectivo! See Adventures in Cuba post for details) and head to Ruta Bikes, where you have reserved a half-day tour that begins at 8 AM.


8:00 AM: Havana Bike Tour and Lunch

Your Classic City Tour with Ruta Bikes begins in the Vedado region of Havana. With a local, English-speaking tour guide, you will bike through the Forest of Havana, the Vedado region, Central Havana, and Old Havana. You may stop at the Plaza Vieja for lunch: check out the La Vitrola restaurant for a quick bite while sitting on the sidewalk people-watching. After leaving Old Havana you will bike back along the El Malecón boardwalk and stop for a fresh glass of juice before returning to Ruta Bikes headquarters.


1:00 PM: Old Havana

Spend your afternoon exploring Old Havana. If you did not get lunch on the bike tour, you may get to Old Havana a little earlier and will have time for lunch then. You can still make your way to La Vitrola, or perhaps instead check out Chanchullero, another great paladar. While wandering around Old Havana, you can visit El Capitolio, the Bella Artes Museum, the Museum of the Revolution, La Floridita (birthplace of the daiquiri and Ernest Hemingway haunt), La Bodeguita (birthplace of the mojito), or the Almacenes San Jose market. Including any and all of these locations in your itinerary should fullfil your visa requirements.


6:00 PM: Dinner

Tonight you have reservations at one of the best restaurants in Havana: La Guarida! Enjoy this fine dinner on the fifth floor of a former colonial mansion in the heart of Central Havana.


7:00 PM: Salsa Lessons and Nightlife

End your day with an AirBNB Experience that includes Cuban salsa lessons taught by locals, followed by a VIP experience at one of the hottest night clubs in Havana. At the open-air Club 1830 you can practice your skills or just enjoy your reserved table as you end your day exploring Cuba.

Tip: if you’re new to AirBNB, use my link to get a $40 credit!

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

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One Day Itinerary for Havana, Cuba

One-Day Bermuda Itinerary

One-Day Bermuda Itinerary

Use the following itinerary to set your schedule for a day of your vacation in Bermuda: this is especially useful for your one full day on the island if you are visiting via cruise ship!

7:00 AM: Breakfast

To see the entire island in one day you’ll need an early start. Grab breakfast either on board your cruise ship or at your hotel. Don’t forget to take a few extra cereal boxes and fruit for snacks throughout the day!

8:00 AM: Depart for the Beach

Purchase your all-day bus pass first thing: you’ll need it to hop on and off the public buses and ferries throughout the day. Take the bus right to Horseshoe Bay beach, one of the quintessential pink Bermudan beaches! If you want a stunning view of the island on the way you can get off a stop early (if coming from the Royal Navy Dockyard) and walk up to Gibbs Hill Lighthouse.

If you’re not ready for the beach first thing in the morning, you may skip this stop and instead visit Tobacco Bay beach at the end of the day. Note that if you choose this second option your timing for the day will be earlier than listed below, leaving extra beach time at the end of the day.

Pink, sandy beaches of Horseshoe Bay

11:00 AM: City of Hamilton

Arrive in Hamilton just before lunch to see the main city on the island. This is a hot spot for shopping, especially for the famous pink sand jewelry sold in a number of jewelry stores around town. Classic vacation souvenirs are also available here, including apparel that can be found in a Vineyard Vines store dedicated almost entirely to Bermuda. You may choose to enjoy lunch at a restaurant along the water, or wait until your next stop to dine at the Swizzle Inn.


12:30 PM: Hamilton Parish

Disembark from the bus at the stop for the Swizzle Inn. Here you can enjoy the infamous rum swizzle right where it was created! The drinks are delicious, but be warned that they are also strong. You can have a full lunch here, or just eat a few conch fritters to hold you over until dinner and temper the drinks.


After your rum swizzle, forego the Crystal Caves and walk over to the Grotto Bay Beach Resort and Spa for some spelunking and cave swimming. Note that the grounds are technically reserved for guests, so to access them you must act as though you belong. Use the path to the left of the front lobby to walk around the building and go down the path towards the water, spa, and caves. The entrance to the cave is well-marked, just before the spa, on your left. The water is somewhat cold but the swim is well worth it! If you continue walking up past the swimming hole there are more caves to explore: the first few are lit but the cave system looks like it could go for miles and could be explored with a flashlight.


Your final stop in Hamilton Parish is another short walk away at the Blue Hole. Enter Blue Hole Park through a parking lot and walk along the path past some caverns until you get to the swimming hole. There is a platform built over the water to stand on and leave your belongings if you decide to venture in. You can enter the water one of two ways: slowly on the left side of the platform or by jumping from the 10- or 15- foot cliffs up the path on the right side of the platform! The water under the cliffs is at least 20 feet deep, and as of October 2017 there were no underwater obstructions. Use the rocks on the other side of the platform to get out of the water and back to your belongings.


4:00 PM: St. George

Take your final bus ride to the town of St. George on the North side of the island. Have a look around the town center, and then head for Fort Saint Catherine. It’s a bit of a hike up to the fort but you should have plenty of time to get there, look around, and get back to catch the last ferry to the Royal Naval Dockyard. If you chose to skip the beach earlier in the day, stop at Tobacco Bay Beach on your way back from the fort for some music, sand, sun, and swimming.

Tobacco Bay Beach

5:30 PM: Royal Naval Dockyard

End your day back at the dockyard where you can explore the shops or take a short taxi ride to Sea Glass Beach to look at the mounds of sea glass on shore as well as the creations left in cement.


7:00 PM: Dinner

Return to your ship if you are on a cruise, or to your accommodations to get ready for dinner and the rest of your evening!

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Itinerary for spending a day in Bermuda traveling the island and seeing all the sites.

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

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One-Day Itinerary for Boston, Massachusetts

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