Beautiful fall views of New Haven and Yale University from the summit of East Rock Park. Image credit Winston Tan via Shutterstock.

Top 7 Places To Visit In Connecticut In The Fall

The colors of fall often mesmerize folks with the red and golden hues of leaves, the crisp air, and the harvest season. The often underrated state of Connecticut is no stranger to this beauty! Featuring both active fall festivities and calm getaways from bustling college towns, these destinations have the best of both worlds and are ideal for a fall on the East Coast. Each destination tells a different story of the culture and landscape of the town. From avant-garde architecture in New Canaan to intricate watersheds developed by Native Americans, these destinations make for gorgeous autumn adventures! 

Sleeping Giant State Park

Fall hike in Sleeping Giant State Park
Fall hike in Sleeping Giant State Park.

Hamden is home to the infamous Sleeping Giant State Park and is located in New Haven County. Hamden is close to colleges such as Yale University and the University of New Haven, making it a relatively populated destination due to its many attractions and natural sites. Sleeping Giant State Park, which is a designated trout management area, is particularly special in autumn. The facilities in the park include bathrooms, picnic shelters, and picnic tables. The park’s peak is on Mount Carmel which is almost 750 feet above sea level and overlooks Long Island and the New Haven skyline. The Sleeping Giant Golf Course is located near the park and is open from 7:30 AM to 6:30 PM. This park has it all! 

East Rock Park

Aerial view of fall foliage in New Haven
Aerial view of fall foliage in New Haven.

Another park located in Hamden is East Rock Park, the largest in New Haven. The park is home to the Soldiers and Sailors Monument and encompasses over 8 miles of hiking trails. The park includes the mountainous ridge of East Rock but does not allow rock climbing. The park earned its name from the formation of Dolerite, a molten rock more resistant to erosion than sandstone. The park is home to Mills River where swimming is prohibited. Frequent hiking trails include Giant Steps Trail which reaches the summit. The Trowbridge Environmental Center is a public nature center that offers educational tours and information about local vegetation and flowers. The Pardee Rose Garden and Greenhouse area grow flowers from early spring until midway through the fall. 

Orange Triangle and Wepawaug Conservation Area

View from the right of Saville Dam in Orange County, Connecticut.
View from the right of Saville Dam in Orange County, Connecticut. 

Located in Orange County, the Orange Triangle and Wepawaug Conservation Area are linked to the Kowal Nature Preserve. The Conservation area allows the entry of leashed pets and allows hiking on designated trails. The most popular trail is the Orange Triangle Trail which passes through a hemlock forest and a bridge over the Wepawaug River which eventually leads up to a vernal pool. The trail does not allow wheeled vehicles. The Whitney Tract passes through another hemlock and crosses into the ravine, a particularly breathtaking experience in the fall! History lovers will delight as the banks of the river on the trail have remains of a mill that manufactured military uniforms during the Civil War.

Indian Rock Shelters Trail

Blue hour after sunset in Madison Connecticut from East Wharf beach
The blue hour after sunset in Madison, Connecticut from East Wharf Beach.

Located in the municipality of Madison, the Indian Rock Shelters Trail passes through rock formations that are unique to the area’s geography. The wetland and climate have led to the formation of ancient granite and embedded quartz. These sites were shelters for native Americans and the area has an intricate watershed system to showcase their rich history and culture. The trail stretches and crosses the Neck River. It is important to note that this trajectory is not recommended as it may be difficult to cross when the water level is high. The final part of the trail passes by the Bartlett Pond, but it is advised to remain on the trail since it becomes very narrow towards the end. 

Bridgeport

Fayerweather Island in Bridgeport, Connecticut, USA.
Fayerweather Island in Bridgeport, Connecticut, USA.

Bridgeport is a great town for those who enjoy festivals. For instance, Bridgeport holds its annual Sound of Sound Music Festival in late September. The town hosts popular artists from pop, country, and rock genres. Other fall attractions in the area include Connecticut's Beardsley Zoo which is infamous for its tiger habitat and various species. The zoo also hosts annual fall festivals such as the Glow Wild Lantern Festival which starts in October and ends in early December. Spooky season in the zoo entails Boo at the Zoo, a longstanding Halloween tradition organized by the Kathy Brady Education Center. 

Danbury

Sign in Elmwood Park with the history of Danbury.
Sign in Elmwood Park with the history of Danbury. Image credit Rosemarie Mosteller via Shutterstock.

Located in Danbury, a city in western Connecticut, The Danbury Railway Museum hosts a collection of fall festivities as well. The town is popular for its train station which commutes passengers to New York and Pennsylvania. The Pumpkin Patch Trains is an annual fundraiser that features local apple cider and cookies. The Story Time Express features a book reading and a 20-minute train ride for kids. Spooky season kits are distributed to passengers and s’mores are prepared on the railroad campfire. These events are held every weekend in October and depart every hour starting noon until 7 p.m. on Saturdays and every hour starting noon to 3 p.m. on Sundays.

New Canaan

Beautiful autumn colored tree with New Canaan's Town Hall
Beautiful autumn-colored tree with New Canaan's Town Hall. Image credit Miro Vrlik Photography via Shutterstock.

The two-day fall fair in New Canaan is held in September. The fair features carousels, ziplines, apple slingshots, spooky strolls, and pumpkin decorating. The fair is held in the New Canaan Nature Center. The town features other sites as well, with Grace Farms holding annual benefits during the fall. The foundation features the River Building which was awarded the Pritzker Prize, as well as other buildings that bring out the town’s topography and greenery. The 80-acre preserve restored 10 biodiverse habitats and features ​​30 weeks of natural-based programming to promote environmental awareness. 

These destinations have a range of experiences that will make the best out of an autumn trip to the “Nutmeg State”. The range of activities that can be had is attributed to the unique terrain of some state parks and different historical backgrounds and social groups specific to the area. This has given rise to various festivities in each town, as well as historical monuments that tell stories of the Civil War and Native American inventions. To fully embrace these fall experiences and scenery, make sure to visit in September and October! 

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