2025's Towns In Connecticut That Come Alive In The Fall
For travelers who love all things cozy and quaint, Connecticut is one of the best places to embrace fall’s charms. Gilmore Girls fans can recall the Hallmark-movie atmosphere of Stars Hollow, the show’s close-knit town and central setting. The Connecticut community, while fictional, embodies the state’s true character: warm hues, even warmer locals, and all the ideals we associate with an idyllic New England autumn.
From its foliage-swathed mountainsides to its spirited festivals, nothing quite compares to the dreamy atmosphere in Connecticut's towns in October and early November. If you want to embrace the state's nostalgia this autumn with apple picking, pumpkin patches, foliage hikes, and fairs, these are 2025's cutest towns in Connecticut that come alive in the fall.
Cornwall
Cornwall may be known as the “Greenest Town In Connecticut,” but in the fall, its hillsides explode with a kaleidoscope of colors. Situated along the Housatonic River and Berkshire Mountains, the town is a gateway to some of Connecticut’s prettiest parks. Mohawk State Forest is especially dazzling this time of year, with Mohawk Mountain ablaze with gold, red, and orange trees. In 2025, ExploreFall’s Foliage Map estimates mid-to-late October is the best time to see Cornwall’s leaves at their brightest.
At Mohawk State Park’s highest point, the 1,683-foot overlook offers panoramic views of the Berkshires below, blanketed with the season’s hues. Around 10 minutes west, sweeping scenes can also be enjoyed at Housatonic Meadows State Park. Along the way, you will pass through the Historic West Cornwall Covered Bridge, a charming local landmark framed by golden trees in the fall. Afterward, Housatonic Meadows hikes like the Pine Knob Loop Trail are a must if you want the ultimate view. This short but challenging trek rewards hikers with stunning vistas high above the tree-dotted river valley.
Kent
Around 12 miles southwest of Cornwall, Kent is another Connecticut town renowned for its vibrant fall foliage. In the years since Yankee Magazine named Kent America’s “Best Fall Foliage Town” in 2010, accolades have continued to pile in, including a high spot on Country Living’s 2023 list of “55 Best Fall Towns in the US For Foliage." Projected to see high colors mid-month and peak vibrancy in late October, 2025 is a great time to witness Kent’s award-winning foliage in person.
Much like Cornwall, Kent’s setting along the Housatonic River brings its postcard New England scenes to life, including the tree-backed Historic Bulls Covered Bridge. Following the river north, Kent’s fiery foliage can also be admired at the Pond Mountain Natural Area and Kent Falls State Park. The latter is the crown jewel of Kent’s park system, showcasing a dramatic multi-step waterfall that plunges over 250 feet into the Housatonic. Although spring produces a stronger cascade, Kent Falls in autumn is absolutely bewitching, its surroundings trees illuminated with yellows and reds.
Glastonbury
Hosting its 50th Apple Harvest & Music Festival in 2025, Glastonbury is a town that loves the nostalgia and tradition of a classic New England fall. The semicentennial celebration will take place from October 17th to 19th at Riverfront Park, a scenic green space along the Connecticut River. According to foliage estimates, the park’s trees will peak from late October to early November, offering the perfect backdrop for Glastonbury’s half-century festivities. Guests can look forward to craft vendors, carnival rides, live performances from local bands, and heaps of mouthwatering apple-themed treats. Notably, the park is also the departing point for Fall-Foliage Kayak Tours with L.L. Bean Outdoor Discovery Programs.
Until October 13th, Glastonbury’s Old Cider Mill is another fun addition for families and apple lovers. Open seasonally, the Mill sells traditional sweet treats like their Natural Apple Cider and Homemade Apple Fritters, along with countless apple varieties from their South Glastonbury Orchard. Kiddos can also enjoy a range of cute and cozy activities at the Mill, from exploring its Corn Maze to visiting its Petting Zoo, which currently features goats, alpacas, rabbits, and a well-fed pot-belly pig named Polly.
Mystic
In fall 2025, the charming seaport town of Mystic will also come alive with apple-themed fun, hosting its 4th annual Mystic Apple Festival. While the celebration is younger than Glastonbury’s, the event will offer its own distinct charms on October 18th or 19th. Showcasing craft vendors and “everyone’s favorite seasonal foods,” guests can shop for everything from hand-knitted crafts to treats flavored with pumpkin, caramel, maple, and the festival’s namesake apple. Better yet, this event will take place at the Olde Mistick Village, offering the ultimate New England setting.
Bordering the Mystic River, the Olde Mistick Village is an open-air, pedestrian mall modelled after an 18th-century Colonial Village. Blending old and new, its old-fashioned storefronts house a range of cozy and unique restaurants and shops, from Deviant Craft Coffee & Donuts to Alice’s Haunted Little Bookshop. Paired with its fall decor, the village trees are set to peak from late October into early November, making Mystic a great town to visit later in the season.
Essex
Driving toward the Connecticut River on the I-95 S, Essex is another timeless New England town with fun for those celebrating later this fall. Much like Mystic, the foliage here will peak around late October to early November, perfectly timed with its Ivoryton Pumpkin Festival. Taking place on October 25th at the Ivoryton Village Green, the celebration will have a mix of Halloween fun and autumn traditions, with something exciting for everyone.
Kid-friendly highlights include a Costume Parade and Trunk or Treating, while all ages can enjoy Horse-Drawn Hayrides and The Great Pumpkin Challenge, a creative carving event with a Pumpkin Lighting finale at 4:30 PM. Additionally, older attendees can discover spookier fun, from Haunted Happenings at the Ivoryton Library to Tarot Card Readings and Tabletop Games, hosted by House of the Triple Moon.
Putnam
Up in northeastern Connecticut, Putnam's peak foliage will fall right in line with its family-friendly autumn festivities on October 18th and 25th, 2025. Brightening downtown, Putnam's Great Pumpkin Festival will celebrate the season with live music, a craft & art vendor fair, and fall-themed activities for kids. One week later, downtown will come alive again with an early Putnam Trick-or-Treat, its merchants and businesses offering candy and goodies to adult-accompanied, costumed kiddos.
For leaf peepers, Putnam’s location along the Quinebaug River is the perfect setting for a serene, bundle-up fall stroll. Running parallel to the racing waterway, Rotary Park can be walked for views of its colorful trees reflected in the water. Studded with crabapples, willows, and pin oaks, the park features a nice range of yellow and red foliage. Further along the Putnam River Trail, pedestrian bridges like the Arch Street footbridge also add a storybook feel.
Bethlehem
Many know Bethlehem as “Connecticut’s Christmas Town,” but before locals start decking the halls, this Litchfield Hills community comes to life with fall festivities. Its north-central setting means foliage here is brightest from mid-to-late October, visible in the hillsides from spots like March Farm. The farm’s Pick-Your-Own season is currently underway, offering hilltop apple and pumpkin picking on Saturdays and Sundays. Guests can also enjoy free wagon rides, a Corn Maze, and cider donuts for sale at the farm’s Market & Bakery.
On October 11th and 12th, the Bethlehem Fairgrounds will also spring to life with their 20th Annual Connecticut Garlic & Harvest Festival. A foodie magnet and vampire repellent, the festival will feature a wide range of traditional and unconventional garlicky treats to sample and buy. From delicious dips and spreads to quirky garlic ice cream, this Bethlehem event is one of the coolest ways to celebrate fall in Connecticut.
Embrace A Stars Hollow Autumn In 2025
The Gilmore Girls town of Stars Hollow may not be real, but it is easy to see why the cozy show chose Connecticut as its setting. The Constitution State boasts some of the best small towns for that quintessential New England atmosphere, boasting rich histories, natural beauty, hospitality, and all the other charms that come with a small-town feel. From Cornwall to Bethelham, these Connecticut communities are gorgeous and full of life year-round, but fall is when they truly shine brightest.
