Fall Festivals in New England: Top 23 Most Unique Spots

Looking to discover the best of fall in New England? You’re in the right place. I’ve got the scoop on the top festivals across:

• Connecticut
• Maine
• Massachusetts
• New Hampshire
• Rhode Island
• And Vermont

From classic fairs to quirky maritime shindigs, there’s so much to do in an autumn visit to New England. Read on and see what makes autumn weekend trips to New England so special!

Ready to discover the best New England Fall Festivals, from Labor Day to November? Let’s get into it:

Quick Hits

• Connecticut:

  • Durham Fair: Think of this as the state’s crown jewel of agricultural fairs. With livestock shows, tractor pulls, and more apple-themed treats than you can shake a stick at, it’s a blast from the past that’s perfect for the whole family.

  • Southington Apple Harvest Festival: This one’s all about apples and community spirit. Expect fireworks, live music, and the best apple pie you’ve ever tasted.

• Maine:

  • Common Ground Country Fair: If you’re into sustainable living, this is your jam. There are workshops on organic farming, plus crafts and yummy local foods.

  • Damariscotta Pumpkinfest & Regatta: Ever seen a giant pumpkin boat race? No? Then you’ve got to check this out. Plus, there are some seriously impressive pumpkin carvings.

• Massachusetts:

  • Topsfield Fair: This fair dives deep into agricultural history. Prize-winning produce, adorable farm animals, and all the fried dough you can eat.

  • The Big E: The granddaddy of them all. It’s like a giant smorgasbord of New England culture with food, music, and enough attractions to keep you busy for days.

Connecticut’s Fall Festivals

As the leaves turn golden and the air gets that nice crisp bite, Connecticut really knows how to celebrate fall. The Nutmeg State bursts with festivals that show off our agricultural roots, community spirit, and love for all things autumn. From big county fairs to cozy harvest parties, there’s plenty to keep you busy.

Two standout events are the Durham Fair and the Apple Harvest Festival. These Connecticut fall festivals are the heart and soul of Connecticut’s fall scene, drawing crowds with their mix of farm exhibits, live music, and delicious seasonal treats. Let’s dive in!

Durham Fair

The Durham Fair is a living history book of the Nutmeg state’s farming past. It’s one of the biggest agricultural fairs in Connecticut, and is packed with fun and learning.

• Livestock Exhibitions: Meet all kinds of animals, from cows to chickens.

• Prize-Winning Produce: Check out the giant pumpkins and other top-notch veggies.

• Educational Exhibits: Learn about beekeeping, sustainable farming, and more.

The fair isn’t just about looking back—it’s a lively celebration of the present and future of farming. You’ll find:

• Live Performances: With four stages, there’s always music in the air. From country to rock, you’ll be tapping your toes.

• Midway Rides: For the thrill-seekers, the rides are a blast.

• Fair Games: Try your luck at winning a prize.

• Farm Museum: Take a stroll through farming history.

Apple Harvest Festival

When it comes to celebrating fall, nothing beats the Southington Apple Harvest Festival. This annual event is a must-see, drawing over 100,000 visitors each year. It perfectly blends small-town charm with big-time fun, capturing the heart of the season.

The festival in Southington, Connecticut, has tons to do. Check out these highlights:

• Fitness Fun: Start your day with a bang by joining one of the exciting road races.

• Live Music: Enjoy performances from talented musicians throughout the festival.

• Arts and Crafts: Admire beautiful works from local artisans at the arts and crafts show.

• Fireworks: As night falls, the sky lights up with a spectacular fireworks display, creating magical memories.

• Apple Treats: Indulge in all things apple—from classic apple pies to unique apple-infused dishes, there’s something to satisfy every craving.

The Stamford Museum and Nature Center Harvest Festival Weekend

If you’re looking for some post-Halloween fun, the Stamford Museum and Nature Center Harvest Festival is the place to be. Held in Stamford, CT, this festival adds a fall twist to an already fantastic spot. You can enjoy apple cider demos, apple slingshots, live animals, crafts, face painting, and more. The best part? Proceeds support the museum’s educational programs.

Maine’s Autumn Celebrations

Ready to head north and experience the magic of Maine in the fall? Maine’s autumn festivals are all about the rugged beauty and independent spirit of the Pine Tree State. These celebrations mix sustainability, local culture, and that classic New England charm. It’s a great way to enjoy the season’s bounty and Maine’s commitment to eco-friendly living and community values.

Whether you’re wandering through inland farms or strolling in coastal towns, Maine’s fall festivals offer a unique glimpse into the state’s rich traditions and stunning landscapes. The air’s filled with the scent of fresh apples, local bands play, and everyone’s soaking up the autumn vibes. Two standout festivals are the Common Ground Country Fair and the Damariscotta Pumpkinfest & Regatta. Let’s dive in!

Common Ground Country Fair

The Common Ground Country Fair, run by the Maine Organic Farmers and Gardeners Association (MOFGA), is no ordinary county fair. This three-day event, set against the backdrop of Maine’s gorgeous fall foliage, celebrates organic agriculture and sustainable living. It runs from September 22 to September 24, 2023, and is all about vivacious communities, local economies, and eco-friendly practices.

Here’s what you can expect to celebrate September in New England:

• Workshops and Demos: Learn about organic farming, sustainable living, composting, and renewable energy.

• Traditional Farming: Watch draft horse demonstrations and see how farming used to be done.

• Exhibitors and Vendors: Over 1000 exhibitors offer everything from hand-crafted jewelry to organic cotton clothing.

• Horse-Drawn Wagon Rides: Take a ride and enjoy a trip back in time.

This year, there’s a new Designated Driver & Minor ticket option, with proceeds going to local organizations. It’s a great way to support the community while having responsible fun.

Damariscotta Pumpkinfest & Regatta

If you want a fall festival that’s totally out of the ordinary, the Damariscotta Pumpkinfest & Regatta is where you need to be. The main draw: giant pumpkin boat races on the Damariscotta River. Yep, people actually carve out huge pumpkins and paddle them like canoes. It’s a hilarious, skillful, and totally unique way to celebrate autumn.

But wait, there’s more! The whole town of Damariscotta turns into a pumpkin wonderland. Giant pumpkins line the streets, each one a masterpiece by local artists. It’s like a pumpkin art gallery right on the sidewalks. You’ll see everything from classic jack-o’-lanterns to elaborate sculptures and scenes, showcasing the incredible talent around here.

Fall for Ogunquit/ OgunquitFest

Ogunquit, Maine is the ultimate fall destination with not one, but two fall events in one weekend! Fall for Ogunquit and OgunquitFest usually happen the weekend before Halloween. Fall for Ogunquit features whoopie pie eating contests, a costume parade, Dogtoberfest for our furry friends, kids’ activities, and an antique car show. At OgunquitFest, you’ll find a huge craft fair with local artisans—perfect for some unique shopping.

Camp Sunshine Pumpkin Festival

In Freeport, ME, the Camp Sunshine Pumpkin Festival lights up the flagship L.L. Bean store campus with over 10,000 jack-o-lanterns! This family-friendly event, held the weekend before Halloween, features live music, a costume parade, and fun activities for kids like movie night. Freeport is about 20 minutes north of Portland, ME, making it a convenient stop if you’re in the area. The town is charming with a mix of shops, and the L.L. Bean campus is always a hit.

Massachusetts’ Festive Fall Fairs

Now, let’s head over to Massachusetts, where the fall fair scene is hopping. The Bay State has a little bit of everything, from huge agricultural exhibitions to quirky Renaissance festivals. One of the biggies is King Richard’s Faire. These events draw crowds from all over and are packed with fun and excitement.

But the state is also home to charming small-town fairs that capture the heart of New England. Take the Sterling Fair, for example. It’s got antique engine shows, helicopter rides, and even a Lego exhibition. Plus, you can shop for local produce, handcrafted goods, and delicious fair food from various vendors.

So, whether you’re up for the hustle and bustle of big festivals or the cozy charm of small-town fairs, Massachusetts has a fall fair that’s perfect for you. Grab your favorite sweater and some friends, and go enjoy the season!

Topsfield Fair

If you want to step back in time and experience a piece of history, you’ve got to check out the Topsfield Fair, the oldest agricultural fair in the U.S. From October 4 to 14 in 2024, this fair will be celebrating over two centuries of New England’s farming heritage. As you wander the fairgrounds, you’ll feel the pride of generations of farmers showcasing their best produce, livestock, and crafts.

Here are some highlights:

• Prize-Winning Veggies: See the best of the best in New England produce.

• Champion Livestock: Meet the animals that have won the hearts of judges.

• Giant Pumpkin Weigh-Off: Growers compete to see who has the heaviest pumpkin. These giants can weigh over a thousand pounds and always get a big reaction from the crowd.

But it’s not all about farming. The Topsfield Fair is a full-on family fun fest with live performances, music concerts, and acrobatic shows to keep everyone entertained. And don’t miss the petting zoo where kids and adults can get up close with farm animals. It’s a great way to connect city folks with the agricultural world.

The Topsfield Fair is a perfect blend of education, entertainment, and tradition, showing why agricultural fairs still charm people today.

Eastern States Exposition

Next is The Big E. Known as the Eastern States Exposition, this is a New England institution. This event near Springfield, MA, is one of the region’s most popular fall attractions. It captures the essence of all six New England states in one place. It’s a grand celebration of New England culture, agriculture, and innovation, drawing crowds from all over.

Here’s what you can look forward to:

• Midway Rides: For those seeking thrills, the rides won’t disappoint.

• Food Galore: From regional delicacies to classic fair food, it’s a foodie’s dream.

• Live Music: Enjoy a diverse lineup of artists keeping the energy high.

What really sets The Big E apart is its dedication to showcasing New England’s agricultural heritage. Each state has impressive displays, giving you a chance to explore everything from traditional farming practices to modern innovations. Whether you’re a New England native or visiting for the first time, The Big E offers an unmatched celebration of the region’s culture, food, and community.

Berkshire Botanical Gardens Harvest Festival

Celebrate the autumn harvest at the Berkshire Botanical Gardens Harvest Festival on October 7-8. This festival has been a beloved tradition for over 80 years. There’s a ton of stuff to do—from face painting and petting zoos for kids to a beer garden for adults. Held on Columbus Day weekend, the festival is set against the beautiful backdrop of the Botanical Gardens.

Enjoy local food and drinks, crafts vendors, a farmer’s market, pony rides, and even a plant sale to spruce up your porch for the season. It’s the perfect addition to a cozy cabin getaway in The Berkshires.

Salem, MA, in October

Salem in October needs no introduction, right? It’s not officially a festival, but it sure feels like one.

If you’ve never been to Salem in the fall, put it at the top of your list. Whether you’re into history (spooky or not), love quaint New England towns, or enjoy great food and historic homes, Salem has it all. It’s one of the coolest things to do in Massachusetts in the fall.

The best reason to visit? All the Halloween vibes you could ever want, including the famous Hocus Pocus filming locations. Even if Halloween isn’t your thing, Salem is still a fantastic place to visit. The fall foliage, historic homes, and charming streets make it worth at least a day trip. It’s one of the best things to do in New England in the fall.

The history of the Salem Witch Trials will give you goosebumps. Plus, there are plenty of haunted walking tours and spooky sites to check out during your visit.

New Hampshire’s Harvest Season Events

Fall in New Hampshire is like stepping into a postcard, with vibrant reds, oranges, and golds lighting up the landscape. The Granite State comes alive with harvest season festivities that showcase local produce and celebrate tight-knit communities. From lively downtown festivals to charming rural gatherings, there’s so much to do.

Here are some must-see fall events in New Hampshire:

• Keene Pumpkin Festival

• Warner Fall Foliage Festival

• Milford Pumpkin Festival

• Sandwich Fair

• Deerfield Fair

These events celebrate the beauty of autumn and New Hampshire’s local culture.

Let’s take a closer look at some standout events:

• Apple Harvest Day in Downtown Dover: This transforms the city into a bustling marketplace with hundreds of crafters, live entertainment, and an apple pie contest that’ll make your mouth water.

• Fall Equinox Fest in Exeter: This festival marks the season change with art, music, yoga, and dance performances.

• Milford Pumpkin Festival: Featuring giant pumpkins, a craft fair, a haunted trail, and a community pumpkin lighting, this one’s a hit for all ages.

Keene Pumpkin Festival

Start with the Keene Pumpkin Festival. This festival is legendary, thanks to its jaw-dropping displays of lit jack-o’-lanterns that turn the town into a magical pumpkin wonderland. As night falls, thousands of carved pumpkins light up the streets, creating a breathtaking sight that draws visitors from near and far.

But it’s not just about the pumpkins. The Keene Pumpkin Festival is a celebration of community spirit and creativity. You’ll find food trucks lining the streets with seasonal treats and comfort foods to keep you going. Local artisans set up booths, showcasing handcrafted wares and unique fall-themed creations. Whether you’re looking for pumpkin jewelry or autumn decor, there’s no shortage of one-of-a-kind souvenirs to take home.

Deerfield Fair

If you’re looking for a classic fall fair experience, the Deerfield Fair is where it’s at. Known as “New England’s Oldest Family Fair,” this event has been a staple in New Hampshire’s autumn scene for generations. It sticks to its agricultural roots, showcasing the best of the region’s farming community. Here’s what you can expect:

• Prize-Winning Livestock: Check out the finest animals in the area.

• Sustainable Farming Exhibits: Learn about eco-friendly farming practices.

• Farm Life Appreciation: Agricultural exhibits show the hard work that goes into putting food on our tables.

• Amazing Food: food vendors sell all sorts of great food

One of the fair’s highlights is the horse shows. From elegant dressage to exciting barrel racing, these events captivate audiences and highlight the bond between humans and horses. And it’s not just about watching—you can get involved too. There are plenty of contests, from entering your best jam in the preserves contest to testing your strength in a tug-of-war. It’s all about friendly competition and fun.

White Mountains Oktoberfest

Head to Loon Mountain Resort on October 7-8, 2024, for the White Mountain Oktoberfest. It’s like having a slice of the Bavarian Alps right in New England. This is the region’s largest celebration of German food, drink, and music. There will be indoor/outdoor beer gardens, a stein-hoisting contest, a keg toss, and plenty of kid-friendly activities. Admission is free, so don’t miss out on this excuse to visit the White Mountains!

Rhode Island’s Coastal Fall Festivals

When fall hits Rhode Island, the Ocean State’s scenic coastline becomes the perfect backdrop for autumn festivals. These special events mix crisp autumn air with salty ocean breezes, celebrating the region’s maritime history and bountiful harvests.

A standout is the Misquamicut Fall Festival in Westerly, Rhode Island. This beachside bash combines a classic fall fair with the vibe of a coastal getaway. Here’s what to look forward to:

• Live Music and Dancing: Enjoy tunes and dancing right on the beach.

• Arts and Crafts: Browse through unique items from local vendors.

• Food Galore: Indulge in a wide variety of delicious eats.

• Midway Rides: For those seeking thrills.

• Classic Car Show: Admire vintage vehicles with the Atlantic Ocean as a backdrop.

In Woonsocket, the Autumnfest offers a more traditional fall fair experience, complete with rides, a food court, and classic car shows. Plus, there’s a Columbus Day parade to enjoy.

Bowen’s Wharf Seafood Fest

If you love seafood, there’s no better place to be in the fall than the Bowen’s Wharf Seafood Fest in Newport, Rhode Island. This event turns the historic waterfront into a seafood lover’s paradise, showcasing the best of the Atlantic. Here are some highlights at what Coastal Living Magazine called one of the 10 Fabulous Fall Festivals on the Coast:

• Lobster Rolls: Succulent and delicious.

• Clam Chowder: Creamy and warming.

• Fried Calamari: Crispy and addictive.

• Oysters: Briny and fresh.

This festival is a culinary tour of New England’s coastal cuisine.

But it’s not just about the food—though that alone is worth the trip. The Bowen’s Wharf Seafood Fest is a full sensory experience capturing the essence of coastal Rhode Island in autumn. As you walk along the wharf, you’ll enjoy:

• Salty Sea Air: Breathe it in!

• Grilling Fish Aroma: Mouth-watering smells.

• Live Music: From sea shanties to modern hits, there’s a lively soundtrack all day.

• Colorful Tents: Adding to the festive vibe.

While seafood steals the show, there’s plenty for everyone, including non-seafood options and dishes for different dietary needs. And don’t forget the drinks—signature cocktails and cold beers flow freely, perfectly pairing with the tasty food.

Whether you’re a seafood fanatic or just want to enjoy the autumn atmosphere, the Bowen’s Wharf Seafood Fest offers a unique and memorable experience.

Autumnfest

As the leaves turn and the air gets crisp, Woonsocket comes alive with Autumnfest. This beloved event is the largest festival in the area, drawing visitors from all over Rhode Island and beyond. It’s more than just a fair—it’s a celebration of community, culture, and the dynamic spirit of New England in the fall.

At the heart of Autumnfest is the grand parade. Marching bands, colorful floats, and community groups wind through the streets, bringing energy and excitement to the city. But the parade is just the start.

During the festival, you can:

• Explore the Craft Fair: Check out handcrafted jewelry, artisanal food, and other unique finds from local artisans.

• Experience the Haunted Trail: Get your dose of seasonal spookiness.

• Enjoy the Talent Show: See local performers showcase their skills.

One of the most anticipated events is the giant pumpkin weigh-in, where growers compete to see who has the biggest gourd. As night falls, the community gathers for a magical pumpkin lighting ceremony, filling the festival grounds with a warm, autumnal glow.

With its diverse activities and focus on bringing people together, Autumnfest truly captures the spirit of fall in New England.

The Jack-O-Lantern Spectacular

One of the most fun things to do in New England in the fall is to check out the Jack-O-Lantern Spectacular. Located inside the Roger Williams Park Zoo in Providence, RI, last year’s event featured over 6,000 hand-carved pumpkins! Each pumpkin is lit with different colored LED lights, making them real works of art. You’ll walk about a quarter of a mile through a path completely illuminated by jack-o-lanterns, making it a super fun family experience.

You can easily combine this event with a trip to Newport, RI, less than an hour away.

Vermont’s Quintessential Fall Celebrations

If you want the ultimate New England fall experience, Vermont is the place to be. It’s a landscape bursting with vibrant reds, oranges, and golds. The Green Mountain State is the perfect backdrop for some amazing autumn festivals. These events reflect Vermont’s deep agricultural roots, strong community bonds, and dedication to local traditions.

From rolling hills to charming town squares, Vermont’s fall festivals let you dive into the state’s unique culture and natural beauty. Whether you’re tasting artisanal cheeses at a harvest fair, watching craftsmen show off their skills, or just soaking in the stunning fall foliage, Vermont’s autumn celebrations offer an authentic slice of New England life.

Here are two must-visit events:

Mount Snow Oktoberfest

A bit of Bavaria comes to Vermont every year! Mount Snow’s Oktoberfest blends New England charm with German traditions. Set against the gorgeous fall backdrop, this festival is a feast for the senses. As you arrive, the smell of sizzling bratwurst and fresh pretzels mixes with the crisp autumn air.

Under festive tents, food and beer vendors showcase their goodies. Beer lovers can sample brews from local favorites like Whetstone Beer Co. and Lawson’s Finest Liquids, and unique offerings from Groennfell Meadery. The food isn’t just German; it reflects Vermont’s diverse and innovative culinary scene.

But Oktoberfest isn’t just about eating and drinking. It’s a full-on celebration of fall in the mountains. You can join in fun contests like stein hoisting, keg tossing, and yodeling. If you prefer something more relaxed, there are plenty of lawn games to enjoy.

And of course, there’s music! Dan Gabel’s Oktoberfest band keeps the party going with traditional German tunes and contemporary hits. Whether you’re a fan of German culture, a beer enthusiast, or just love the beauty of Vermont in the fall, Mount Snow Oktoberfest is an unforgettable experience.

Stowe Foliage Arts Festival

As the leaves hit their peak colors, Stowe, VT, becomes an art lover’s paradise during the annual Stowe Foliage Arts Festival. This annual celebration is a must-visit in Vermont, blending artistic flair, delicious food, and stunning natural beauty. And the Green Mountains will be decked out in stunning autumn colors—it’s a feast for the eyes, both on and off the festival grounds.

At the heart of the festival is an impressive showcase of artisans from New England and beyond. You can browse through all sorts of handcrafted goodies, including:

• Intricate Jewelry

• Fine Art

• Functional Pottery

• Cozy Textiles

The best part? You can often watch the artists in action, getting a sneak peek into their creative process.

As you wander through the festival, you’ll be tempted by the aromas of seasonal treats. Here’s what you can expect:

• Local Food Vendors: Think apple cider doughnuts and hearty soups to warm you up on a crisp autumn day.

• Live Music: Enjoy tunes from local musicians as you explore.

• Unique Finds: Don’t miss the Vermont Country Store for traditional and unique Vermont items.

Whether you’re an art collector, a craft enthusiast, or just someone who loves the beauty of fall in New England, the Stowe Foliage Arts Festival offers the quintessential Vermont autumn experience.

Billings Farm And Museum’s Harvest Celebration

If you’re in the mood for some traditional barn dancing, live music, pumpkin bowling, and crafts, head to Billings Farm and Museum in Woodstock, VT. You can take a wagon ride through the pastures, husk and shell corn, and press apples into cider. And the best part is that it’s all surrounded by beautiful fall foliage, during it’s October 7-8, 2024 run.

But please, don’t forget to try the cheese—it’s delicious!

More Things to do in New England in the Fall

While New England’s fall festivals are a seasonal highlight, there’s so much more to explore. If you’re looking for a serene retreat, head to Provincetown at the tip of Cape Cod. Here, you can visit historic lighthouses, trek across windswept sand dunes, and enjoy various festivals that extend into the holiday season. The off-season vibe means fewer crowds and a more personal experience of this charming seaside town.

For the foodies out there, autumn in New England is a culinary delight. Take a drive along the Vermont Cheese Trail, where you can visit:

• Small Family-Owned Farms: Taste the love in every bite.

• Larger Operations: Enjoy formal tours and sample artisanal cheeses.

If you want to sharpen your cooking skills, check out workshops or wine tasting dinners at spots like The Inn at Hastings Park or Ocean House. Learning from expert chefs in a cozy New England setting? Yes, please!

Nature lovers, there’s plenty for you too. Here are some great options:

• Hiking: From the rugged trails of Maine’s Baxter State Park to the more accessible World’s End Reservation near Boston.

• Zip Line Adventures: For a unique view of the fall foliage, try Gunstock Mountain Resort in New Hampshire or Catamount Mountain Resort in the Berkshires.

• Whale Watching: Head to Cape Ann or Cape Cod for a chance to spot these majestic creatures from October through early November in New England.

• Corn Mazes: Hit-up the CT corn mazes, or make the trek to the largest corn maze in New England, the Great Vermont Corn Maze

History buffs, don’t worry—we’ve got you covered too. In Massachusetts, the Trustees of Reservations manage several historic sites and museums, including the picturesque World’s End Reservation and the enchanting Naumkeag Pumpkin Show.

For a truly unique fall experience, consider a cranberry harvest tour at A.D. Makepeace Company in Wareham. Witness the bogs flooding and the collection of these tart berries firsthand. It’s an experience you won’t forget!

Tl;dr

New England’s fall festivals are the best way to soak up the season. Each state brings its own flavor, showcasing the rich harvest, stunning foliage, and a strong sense of community in various cute New England towns. From the Keene Pumpkin Festival to the Bowen’s Wharf Seafood Fest, and the Stowe Foliage Arts Festival, there’s plenty to do. But the fun doesn’t stop at festivals. Scenic drives, hiking trails, historical tours, and culinary adventures are all part of the autumn magic here. These activities give you a taste of the heart and soul of New England, making it a must-visit destination in the fall.Frequently Asked Questions

When is the best time to visit New England for fall foliage?

The best time for fall foliage in New England is from late September to mid-October, with coastal areas peaking a bit later than inland regions. Plan your trip to catch the fall colors!

Are these fall festivals suitable for families with young children?

Absolutely! Most New England fall festivals are great for families, with activities like petting zoos, kid-friendly rides, and special children’s events.

Do I need to buy tickets in advance for these festivals?

Yes, it’s a good idea to buy tickets in advance for popular festivals like The Big E or the Common Ground Country Fair to avoid long lines and ensure entry, especially during peak times.

What should I wear to a New England fall festival?

Dress in layers, wear comfortable walking shoes, and bring a light jacket or sweater since the weather can be unpredictable. And don’t forget to check the forecast before you go!

Are there accommodations near these festivals?

Yes, there are plenty of accommodations near the festivals, but it’s best to book early as rooms fill up quickly during peak foliage season.