Scenic drives to admire the Connecticut fall foliage include the Long Island Sound Coastal Roads and the Litchfield Hills in northwestern Connecticut. These areas offer the perfect background for a dramatic scenic drive in Connecticut at any season.
However, for me, the trip that comes alive in the fall is nestled in the East Connecticut “Quiet Corner”: Route 169. This is the crown jewel of all the fall foliage scenic drives in Connecticut. Let me take you for a quick ride!
The peak Connecticut fall foliage season typically begins in mid-October and continues until the end of October. Sometimes, you can go on an autumn scenic drive in Connecticut even in early November. That is because Connecticut has a milder climate than many other parts of New England, as shown by the plethora of wineries and vineyards you’ll find these days in the region. Since you’ll be passing by many of them, you might as well go for a visit or a wine tasting (if you’re not the driver!).
The route to see the best fall foliage in Connecticut
Traveling Route 169 is just as much about old buildings and neighborhoods with traditions as it is about the brilliant fall colors shift – even though you’ll be blessed with plenty of chances to soak up color and take an eye-popping, memorable snap.
Our scenic drive in Connecticut runs parallel to Route 169 from Lisbon, CT, all the way to the Massachusetts border. While it’s only a short drive of just over 30 miles, you’ll see that it will cover a lot of places that offer the best spots to admire Connecticut fall foliage.
Start your scenic drive in Connecticut in the city of Lisbon, which can be reached from I-395 exit 83A. The center of the city is known as Newent. Visit the John Bishop Museum and the Newent Congregational Church while you’re in town for a sample of some of the architectural styles in the Connecticut area. You can also sample the local wine at the John Palmer House Heritage Trails Winery.
Follow Route 169 from Lisbon / Newent and travel 8 miles to Canterbury for some more Connecticut fall foliage views.
John Bishop Museum
Address: 11 CT-169, Lisbon, CT 06351 | See on map
The Newent Congregational Church
Address: 12 S Burnham Hwy, Lisbon, CT 06351 | See on map
John Palmer House Heritage Trails Winery
Address: 4314 N Mississippi Ave, Portland, OR 97217 | See on map
Named after the Cathedral City of Kent, England, Canterbury was initially settled in 1697. A visit to this area to admire Connecticut fall foliage will also provide you with a glimpse into the state’s early American past. Highlights are the iconic New England City Green and the Prudence Crandall Museum.
Prudence was an exceptional woman, and the Prudence Crandall Museum records her effort to provide education to black women during a time of violent injustice. Prudence’s neighbors and peers ultimately ostracized and forced her to close her school and leave the city to never return.
Wrights Mill Tree Farm is a pick-your-own town favorite, and during the Connecticut fall foliage season, it offers a spooky hayride and a chance to pick your own pumpkin. This 250-acre farm is situated at the north end of Canterbury.
From Canterbury, drive 7 miles to Brooklyn for more Connecticut fall foliage. Along the way, you’ll pass by beautiful farms and houses set among the rolling hills and fields of the area.
Prudence Crandall Museum
The Prudence Crandall Museum is CLOSED for renovations. The Museum is scheduled to reopen sometime in 2021, although an official date has not yet been determined.
Address: 1 S Canterbury Rd, Canterbury, CT 06331 | See on map
Tel. +18605467800 | Website
Wrights Mill Tree Farm
Open Sunday-Thursday between 09.00 and 17.00 and Friday-Saturday between 09.00 and 11.00.
Address: 65 Creasey Rd, Canterbury, CT 06331 | See on map
Brooklyn has been steeped in tradition. Here, you can discover lots of beautiful historic buildings, most of them located in a 1.75-acre area known as Brooklyn Green. Both Brooklyn and Brooklyn Green are registered in the National Register of Historic Districts.
The sights include the Friendship Valley Inn, the Underground Railroad Station, where Prudence Crandall took refuge during her trial, and the 18th century Old Brooklyn Burial Ground. The nearby C. Vaughan Ferguson Jr. Conservancy and Lester B. Williams Memorial Forest is the place to go for a walk on trails between marshlands and hills.
The best way to visit Brooklyn Green is to park your car and go for a walk. With five churches on the green and a cluster of historic houses, monuments, and memorial stones, something is bound to catch your attention for further exploration. It’s an interesting visit at any time, but the Connecticut fall foliage makes for a wonderful backdrop!
Friendship Valley Inn & Underground Railroad Station
Address: 60 Pomfret Rd, Brooklyn, CT 06234-1815 | See on map
C. Vaughan Ferguson Jr. Conservancy and Lester B. Williams Memorial Forest
Address: 41.806490, -71.952575 | See on map
4. On the way to Pomfret
Leaving Brooklyn on Route 169 and heading north towards Pomfret, you can pass by the 200-acre Lapsley Orchards in the historic district of Bush Hill. Here, during the fall, you can pick crisp apples or buy the perfect pumpkin for your front porch.
Another side trip worth taking before you get to Pomfret is Mashamoquet Brook State Park. At the intersection with Route 101, head west and take the entrance to the park less than a mile down Route 101. With the abundance of maples and oaks in the forest, the Connecticut fall foliage is dazzling here.
Make sure you take a short walk to the Israel Putnam Wolf Den while you’re in the park. There, you’ll find a plaque illustrates the events leading to the death of the last wolf in Connecticut.
Open daily between 10.00 and 18.00.
Address: 403 Orchard Hill Rd, Pomfret Center, CT 06259 | See on map
Mashamoquet Brook State Park & Israel Putnam Wolf Den
Open daily between 08.00 and 20.00.
Address: 276 Mashamoquet Rd, Pomfret Center, CT 06259 | See on map
Back on Route 169, continue your scenic drive in Connecticut to the middle of Pomfret. A walk across Pomfret offers another opportunity to see the 18th-century Sabin Cemetery, the 19th-century churches, and the 13th-century French window at the Pomfret School Chapel. Pomfret is also home to Sharpe Hill Vineyard, one of the wineries on the Connecticut Wine Trail, and is available for touring and wine sampling.
Sabin Cemetery (or South Cemetery)
Address: Pomfret Center, CT 06259 | See on map
Pomfret School Chapel (Clark Chapel)
Address: 34 Kings Hwy, Pomfret Center, CT 06259 | See on map
Continue north on Route 169 from Pomfret to Woodstock, the final leg of this autumn scenic drive in Connecticut. Before you reach the picturesque New England village of Woodstock, you will have the chance to discover several more hiking trails at The Connecticut Audobon-Pomfret Farms and The Air Line State Park Trail.
Besides the autumn foliage, Connecticut is rich in museums and historic houses, and in Woodstock, they all come together at the Roseland Cottage – a striking pink Gothic Revival style house that is also home to the Bowen Museum. The house has original furniture and tours are provided from June to October.
Woodstock has a traditional New England town feel, with a green village lined with maples and an ancient burial ground, a meeting house, and several 18th-century homes on the perimeter.
If you decide not to return on the same day but to relax in Woodstock for the evening, then I know where you can find suites and rooms with cozy fireplaces. The Inn at Woodstock Hill is on the National Register of Historic Places and is a fitting final stop to this scenic drive in eastern Connecticut. It’s also near some of the best foliage views in the area.
The Connecticut Audobon-Pomfret Farms
Address: 218 Day Rd, Pomfret Center, CT 06259 | See on map
The Air Line State Park Trail
Open daily between 07.00 and 18.00.
Address: 69 Smith St, East Hampton, CT 06424 | See on map
Address: 556 CT-169, Woodstock, CT 06281 | See on map
As you drive along Route 169, keep your eyes open for antique shops and bargain stores in towns and villages. Connecticut is the unofficial antique capital of New England, and on your scenic drive in Connecticut, you’re bound to discover the perfect treasure to bring back home.
Traveling on Connecticut’s Route 169 is a beautiful drive in New England at any season. However, a scenic drive to admire Connecticut fall foliage is ideal when the scent of autumn fills the country farms and villages along the route. Fall in love with the splendor of the peak color season in Connecticut this fall!
Connecticut fall foliage route by…
Cristina Popescu is a Romanian blogger who has been traveling since 2008. She has visited 100+ countries across all the continents and accumulated firsthand knowledge about beautiful travel destinations. There is nothing she won’t try at least once in a lifetime and she wishes to encourage others to get out and see the world, too.
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