Aerial view of a tower that sits on the Talcott Mountain State Park in Simsbury, Connecticut.

These Small Towns In Connecticut Come Alive In The Fall

Thinking about doing a little scenic fall travel? Look no further than the beautiful state of Connecticut. Although the scenery can vary slightly each year, Connecticut's fall colors are typically most vibrant from early October to early November, making it the most ideal time to visit. Not only are the trees picture-perfect with their leaves of gold, crimson, and orange, but the state's small towns also come to life during the fall months with festivals and activities that celebrate the season. No matter where visitors may find themselves in this Northeastern state, there will be a small town offering festivals, pumpkin patches, apple orchards, and all things autumn!

Monroe 

Landscape fall scene featuring concrete bridge in Monroe
Landscape fall scene featuring concrete bridge in Monroe.

Monroe is the quintessential quaint northeastern town, complete with family-friendly activities, many outdoor spaces, and fall fun for all ages. Nearby Beardsley's Cider Mill and Orchard is the perfect place to begin your autumn visit to Monroe. The fall-inspired attraction allows visitors to pick their apples from a wide selection of varieties, such as Jonagold, Winesap, Braeburn, and Red Delicious. The orchard also features an onsite cider mill and bakery, so make sure to pick up some treats for home! When it comes to exploring local nature, Great Hollow Lake is the ideal spot for basking in fall colors in all of their vibrant glory. 

Mystic 

Panoramic view of residential homes by the Mystic River during a vibrant sunrise.
Panoramic view of residential homes by the Mystic River during a vibrant sunrise. 

The quaint coastal village of Mystic is the perfect place to catch cool, crisp ocean breezes and beautiful fall colors. Located in the northern region of the state, Mystic features everything from a charming downtown full of unique shops and cafes to vineyards and breweries. The Denison Pequotsepsos Nature Center treats visitors to a palette of fiery fall colors, as well as the annual Spooky Nature Trails Halloween event. The woodland trails glow with carved jack-o-lanterns, and ghost and goblin stories delight kids of all ages. Visitors can also take a trip to the Mystic Seaport Museum or the Olde Mistik Village, a bustling outdoor shopping mall.

Old Saybrook

Old Saybrook Shoreline, Connecticut
Old Saybrook Shoreline, Connecticut.

Settled in 1635, charming Old Saybrook is one of Connecticut's oldest towns. Situated where the Connecticut River joins the Long Island Sound, this town is a water lover's paradise. The small town comes to life during the fall, when its verdant landscape transitions into autumnal shades of crimson, gold, and orange, and local festivals give the area a celebratory vibe. Saybrook Point Park, which offers views of the Connecticut River, is ideal for a crisp fall walk or picnic, while the Great Cedars Conservation Area beckons visitors with its 300 acres of open space and miles of hiking trails. 

Essex

Waterside houses and boats moored in Essex, Connecticut, on an autumn day.
Waterside houses and boats moored in Essex, Connecticut, on an autumn day.

Another scenic and festive small town to spend a day or two in is Essex, which is also located on the Connecticut River. On a warm fall day, visitors can view the charming town from the water, aboard a schooner cruise or eagle boat tour. For those who prefer to stay on land, the Bushy Hill Nature Preserve is ideal for exploring local wildlife and seeing the fiery fall foliage. The Canfield-Meadow Woods Nature Preserve offers miles of hiking trails, while Viney Hill Book Preserve offers a few ponds and picnic areas for an outdoor autumn lunch with family and friends.

Litchfield 

Saville Dam on a sunny fall day in the Litchfield Hills.
Saville Dam on a sunny fall day in the Litchfield Hills.

Named a "Top Small Town Destination" by Smithsonian Magazine, Litchfield has the perfect combination of natural beauty, rich history, outdoor recreational opportunities, and culture. Although visiting here makes for a great escape any time of the year, the small town comes to life in the fall, when the vibrant colors light up the landscape. Featuring a quaint English Tudor-style cottage at its centerpiece, Topsmead State Forest is the ideal starting point during an autumn adventure. The 4,000-acre White Memorial Conservation Center is another top-notch fall destination, as visitors can explore its 40 miles of trails, Bantam Lake, and an onsite nature museum. 

Guilford

View of signs and white barn for Bishop's Orchards market.
View of signs and white barn for Bishop's Orchards market.

A charming small coastal town nestled on the Long Island Sound, Guilford offers everything visitors could want in a fall getaway. Each October, the town hosts the Fall Food Festival and Expo, which draws in visitors from all over, and the weekly Farmers Market at the Guilford Fairgrounds tempts foodies with its homegrown fall produce and locally produced goods. You won't want to miss a trip to Bishop's Orchards, where you can pick your apples, and treat your family to a pumpkin patch, corn maze, and other fall-inspired activities. The Braemore Preserve, Jared Eliot Preserve, and the Genesee Recreation Area are all perfect places to take in the area's vibrant fall colors. 

Simsbury

Aerial view of tower sits on the Talcott mountain state park in Simsbury, Connecticut.
Aerial view of the tower sits on the Talcott Mountain State Park in Simsbury, Connecticut.

With its quaint downtown filled with historic houses and bustling shops and cafes, position on the scenic Farmington River, and endless recreational opportunities, the small town of Simsbury doesn't disappoint autumn visitors. A climb to the top of the 165-foot Heublein Tower in Talcott Mountain State Park gives visitors a spectacular view of fall foliage in all directions. The woodland trails in the 370-acre Massacre State Forest also give fall adventurers a unique autumnal view and are home to the Great Pond, the town's largest body of water. 

For folk who are lucky enough to find themselves in Connecticut this fall, do not miss an opportunity to visit one of these scenic small towns for an authentic autumn experience. The towns' warm, welcoming vibes blend breathtaking beauty with the season's cool, crisp air, giving these destinations a cozy, festive, feel. Whether you desire a colorful walk through the woods or a day at a family-friendly pumpkin patch, Connecticut has what you are looking for. 

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