New England Fall Activities, Planning Your Bucket List Destination

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Riotous color, historical surprises, and dark night skies and some not-so-traditional sights and sounds of the season—New England fall activities are a delight that you’ll want to add to your travel bucket list.

We’ve curated a list of the best activities across the region to get you on your way and help you enjoy the singular experience of autumn in New England.

Harvesting New England Fall Bounty

Apples growing in an orchard, representing one of the most iconic New England Fall activities.
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There are few places in the world where the fall season ushers in the same magnitude and beauty as you’ll see when traveling from Connecticut through Massachusetts, Vermont, New Hampshire and Maine. Cornflower blue skies are the perfect backdrop for the resplendent carpet of autumn hues that blanket hillsides and valleys as warm days give way to cool nights.

New Englanders have learned to welcome the end of summer despite the portent of bitter cold waiting just around the bend, glorying in autumn’s bounty with a full slate of New England fall activities. Many celebrate the harvest, harkening to the early days of settlement when a bounteous crop meant winter survival.

Apple picking remains a favorite fall pastime with apple orchards nearly as proliferous as autumn leaves. Our usual favorite is Lost Acres Orchard in Granby, Connecticut. This small family-run orchard offers pick-your-own and pre-picked apples in a number of varieties as well as a bounty of cider and exceptional baked goods. Head over at lunch time and enjoy a scrumptious farm-cooked meal on the outdoor covered patio. Weekends welcome hayrides and a chance to watch the cider pressing in action.

Another favorite for family fun is Karabin Farms in Southington, Connecticut. Due to COVID-19, hayrides have been shelved and the petting zoo closed, but pick-your-own fruit is available if you don’t mind a quick stroll into the orchard. The farm store, featuring home-grown meats and delectable delights also remains open.

There are few New England treats as quintessential and revered as the apple cider donut, and Red Apple Farm in Phillipston, Massachusetts offers an award-winning culinary experience. In fact, you can make a day of it at Red Apple Farm, picking apples, visiting the farm store and sealing the deal with a fresh plate of home-smoked barbecue perfectly paired with the hard apple cider or local brews. Enjoy live music on select weekends while reveling in the perfect view of the fall color over Wachusett Mountain.   

For a harvest of a different kind, why not try cranberries. There are few places outside of New England where you can tour a working cranberry farm and join in the fun of the harvest. Cranberry Bog Tours offers just such an experience, taking visitors out onto a working bog to learn about one of New England’s most historic industries. It’s a new way to view the colors of the season as cranberries begin ripening for harvest beginning in September.

Autumn Outside the Ordinary

If you’re looking for a way to soak up all that magnificent regional fall beauty while experiencing something new, you’ll find an A-list of fall activities in New England to meet your goals. Start with the Mount Washington Cog Railway, where steam engines chug the three and a quarter miles to the summit of New Hampshire’s Mount Washington. That’s a steep 25 percent grade you’re covering to reach the 6,288-foot summit, so sit back and let someone else do the work.

Mount Washington is part of New Hampshire’s White Mountain range, once one of the most popular tourist destinations for New England travelers. While in the area, there are other ways to enjoy the colors of nature, such as a scenic chairlift at Cranmore Mountain Resort. Once you reach the summit, take in a meal at the historic Meister Hut and enjoy a different view of Mount Washington.

To kick your scenic viewing into high gear, head over to Backyard Adventure Tours in Canaan, Connecticut. You’ll revel in the full-throttle feel of your personal UTV as you hit the open trail, splash through streams and scream down hills. In fact, you might find you miss some of the color whizzing by, but you won’t regret it immersed as you’ll be in all the off-road excitement.

For an historic perspective on New England fall, take a time machine back to a colonial town and join the people at Sturbridge Village in Massachusetts. Costumed historians bring the past to life in this immersive encounter of days gone by.

Fall is an especially interesting time to visit as Phantoms and Fire welcomes visitors after hours to explore the creepy side of Old New England in the dark.  Witness the horrifying tales of Edgar Allen Poe as you’ve never seen them before or take a scavenger hunt for sweet surprises.

Given its witchy history, it’s no surprise that Salem, Massachusetts also comes alive with haunting surprises as fall winds down, and the 1692 Salem Witchcraft Walk tour is the perfect way to learn the stories of the accused while visiting actual sights, such as the Old Burial Ground Cemetery. A separate candlelit walking tour of the streets still lined with vintage buildings is the perfect way to cap off your day.

Fall Fun on the Coast

Whale watching off the coast of Cape Cod is a perfect New England Fall activity as sightings are plentiful.
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As the weather turns cooler, New England beaches empty out, making room for the heartier visitor to get a glimpse of one of the region’s most notable attractions—the Atlantic Ocean. It’s a great time to stroll the sand with your furry friends as dogs are prohibited on most beaches during the warmer weather.

If your feet are tired from traipsing all those trails in search of leaf popping glory, then leave the walking to a four-legged friend of another kind and explore the beach on horseback. C and L Stables in Warwick, Rhode Island takes equestrians with some experience to hidden beach sites. For a less strenuous adventure, Rustic Rides on Block Island welcomes riders of all abilities to join in the beachcombing fun.

Leaving the shore and braving the waves by boat gives you the chance to commune with one of the denizens of the deep. October is one of the best times for whale watching off the coast of Cape Cod, and thinning summer crowds mean you won’t have to fight for a spot at the rail to see the magnificent sites. Humpbacks have been known to make regular appearances through November, so check with one of the local whale watching outfitters for the best time to tour.

Glorying in Harvest Fun

Early settlers to the New England territories relied on the harvest to sustain them as the winter winds howled and snow piled up by the foot. These days, New Englanders still welcome the end of summer by celebrating a good crop, but it’s mostly symbolic as pumpkins, mums and corn stalks become the harbinger of the season’s change.

The Boys and Girls Club of Milford, Connecticut has a long-standing New England fall activity tradition, celebrating the harvest bounty with Pumpkins on the Pier. This festival of fall favorites includes everything pumpkin, from crafts, activities, games, and of course amazing pumpkin displays lining the town pier.

For pick your own fun, take a jaunt out to Castle Hill Farm in Newtown, Connecticut where you should have no trouble finding the most spectacular orb from over 4 acres of vines. Hayrides open in October, and for a festive way to spend all Hallows eve, why not pack up your flashlight and head out to Castle Hill’s nighttime corn maze. What we love about Castle Hill is that they welcome your canine buddies as long as they are friendly and you’re willing to clean up after them.

If you’re out and about enjoying the fall colors to the north, try Hathaway Farm and Corn Maze in Rutland, Vermont, voted the number 2 corn maze in the nation and Yankee Magazine’s number one choice in 2012. Each year, the folks at Hathaway dream up something special for fall travelers and then deliver it across a 13-acre maze. Clues will guide you across 3 bridges and out over wondrous views of the Vermont countryside.

When you’ve found your way out to civilization again, stop at the livestock barn to see Petunia and Penelope, the pot belly pigs, or to give Flossie the cow a scratch behind the ears. From there, join a one-of-a-kind New England fall activity and jump into a corn pit or simply soak up the fall color by enjoying a wagon train ride around the farm.

New England Fall Activities – Festivals and Fairs Abound

dachshund on pumpkins at New England fall fair, one of New Englands fall activities.
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Given the area’s farming heritage, it’s no wonder that New England’s slate of fall activities includes a full slate of fairs across the four states. Of course, the granddaddy of them all is the Eastern States Exposition, more commonly known as the Big E. Each year, beginning in mid-September, the fairgrounds in Agawam, Massachusetts open their doors, saying goodbye to summer with a full slate of fall fun.

You’ll find livestock on display as well as arts, crafts and the ever-present new mop of the year. You can enjoy native edibles from each of the state pavilions as well as state-inspired art and other cultural displays. We usually make our way directly to the Maine pavilion, grab a lobster roll and then begin our stroll through the buildings. Then it’s off to watch the chicks hatch and to grab an éclair.

While the Big E offers the largest in fair delights throughout New England, individual counties and towns have also been known to put on a good show. Here are some of the largest and most well-recognized throughout the New England States:

Connecticut

Durham Fair

Sept. 23-26

Highlights: first class animal competitions and exhibits, carnival rides and games on the midway

Maine

Fryeburg Fair

Oct. 6-10

Highlights: livestock shows, harness racing, horse pulling culinary contests and a skillet toss

Massachusetts

Nantucket Island Fair

October 2-3

Highlights: Canine competitions (see how much you look like your dog), livestock shows, pumpkin and scarecrow contests, animal exhibits

New Hampshire

Deerfield Fair

Sept. 30-Oct. 3

Highlights: Livestock pulls, demolition derby, sheep shearing, live entertainment

Nothing says fall more unequivocally than pumpkin, and the folks in Dariscotta Maine know how to serve it up with flair. The Pumpkinfest and Regatta elevates the orange orb to a new status, offering sidewalks lined with decorated pumpkins and the chance to pilot your own pumpkin craft and race your way to fame in the Pumpkin Regatta. Unfortunately, the Regatta has been cancelled in 2021, but let’s keep our fingers crossed for its return next year.

Visit the Last Dark Sky on the Eastern Seaboard

Milky Way over Acadia
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Acadia National Park in northern Maine is one of the region’s most famous destinations for travelers seeking New England Fall beauty, and while millions of travelers a year can’t be all wrong, it’s possible that they’re missing out on one of the park’s little known autumn treasures. The Acadian Night Sky Festival usually runs the last weekend of September, celebrating the darkest skies on the eastern seaboard.

Borne of the local community’s enthusiasm to preserve the night skies over Mount Desert Island, The Acadia Night Sky Festival celebrates the local commitment to starlight preservation and affords the visitor an unparalleled opportunity to glimpse the Milky Way in all its fall splendor while learning about dark sky conservation. It’s one of the best of New England Fall activities and the perfect way to cap off the summer.

Photographers beware, this is one event you don’t want to miss. For a full list of happenings, visit the organizational calendar.

New England Fall, It’s the Best Time of Year for Food

Fall in New England serves up some of the region’s most iconic fare, celebrated through festivals and culinary contests. One of the most celebrated takes place in October as travelers join locals to learn about shellfish of the Massachusetts coast. Oysterfest in Wellfleet offers shellfish farm tours, culinary delights featuring the famed oyster as well as the chance to win $1,000 in one of the region’s only oyster shucking contest.

If you’ve never heard of a Fluffernutter, you probably aren’t alone. The regional sandwich, comprised of peanut butter and marshmallow fluff, might not be world renowned, but it is a New England staple, and one of the few iconic foods to get its very own festival.

What the Fluff takes place in late September, sharing and commemorating just about anything related to marshmallow fluff, but particularly the peanut butter and fluff creation. You’ll find fluff just about everywhere you go in Somerville during the festival and also have the opportunity to test your fluff trivia knowledge.

When you live in York, Maine, harvest takes on a different meaning than it does in other parts of the country. Instead of bringing in the sheaves, locals celebrate the bounties of the sea. Harvestfest takes place on the beach each October where the York Elks Lodge serves up lobster, crab and tuna rolls. For more mouth-watering seafood served on the beach, the Hampton Beach Seafood Festival takes place in New Hampshire in September.

While New England is home to a number of food festivals, such as the Boothbay Harbor Fishermen’s Festival and the Whoopie Pie Festival, many events have been cancelled again in 2021. Let’s hope for a safer and more eventful fall in 2022.

Fall Hiking in New England

If you’re looking for fun things to do in New England, hiking is a good bet any time of year, but takes on new meaning as the leaves begin to turn and simple hillsides become glorious patchworks of color. Strike out in any direction, and you’re certain to find sights and sounds to please the senses. However, if you’re looking for grand vistas and the most stunning displays of color, you can’t beat the hikes below.

The Heublein Tower hike takes off from Simsbury, Connecticut, traverse a steep climb a traprock ridge where sturdy adventure-goers can see color into the neighboring towns. But ridge view vistas are not the only thing this hike has to offer. Continue along the trail to reach the tower itself, where a quick climb to the top reveals that fall color and beauty is alive and well in the neighboring states of New York and Massachusetts.

Immerse yourself in the beauty of fall while walking old carriage trails at this historic driving park. While the stone roadways are gone, rock walls and wide paths remain, as well as the waterfall dam built during the turn of the 20th century. In addition to historic sites amid changing leaves, you’ll also be treated to views of Hartford, nestled in the changing leaves at Case Mountain Preserve in Manchester, CT.

In the summer, the Ice Glen trail in the Berkshires of Massachusetts is like a fairy world, complete with hidden underground lairs and natural stone pathways, but in the fall, the trail offers autumn splendor as the greenery turns rich shades of amber, red and gold.

For a quick jaunt to scenic views, visit Haystack Mountain in the northwest corner of Connecticut. A quick hike leads to a ridgetop tower. You won’t see much from the ground, but climb the stairs inside and a new world of color emerges as you look out over the hills of Connecticut and the Taconic Mountains of New York.

If hiking is your passion, be sure to watch for our book on New England hiking to be released in early 2022. We’ll be covering the hidden gems of southern New England and embarking on trails most visitors to the states of Connecticut and Massachusetts will never find in popular guide books. To be alerted to its release, sign up below.

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Kathleen Hesketh

Kathleen is a travel agent with Mickey World Travel, a platinum level Authorized Disney vacation planner, where she helps people discover the magic of a Disney vacation and other travel destinations. She is also the chief author and editor for Seconds to Go - a travel blog where she shares experiences from traveling the U.S. with her daughter, Ali.
Mother daughter travel bloggers exploring the U.S.

We're Kat and Ali, a pair of mother-daughter travel bloggers exploring the U.S. We're sharing our experiences, tips and insights to help you more easily get out and explore the beautiful landscapes and places of this nation.

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