This scenic fall foliage trail runs south to north in Connecticut’s eastern corner along Route 169. Peak fall foliage in Connecticut generally begins in mid-October and lasts through late October.
Traveling Route 169 is as much about historic buildings and communities with traditions, as it is about brilliant color changes, though you will also be blessed with many opportunities to peek into the leaves.
The trip follows Route 169 from Lisbon, CT, to the Massachusetts border – a short trip of just over 30 miles, but as you’ll see, it packs a lot into a small area.
Let’s turn the ignition on and get moving …
You will begin this scenic drive in the city of Lisbon, which can be reached, from Exit 83A of I-395. The center of the city is known as Newent.
Visit the Bishop House Museum and the Newent Congregational Church to learn about some of the architectural styles that you will become familiar with during this tour.
Take Route 169 from Lisbon / Newent and drive the 8 miles to Canterbury.
Named after the cathedral city in Kent, England, Canterbury was originally established in 1697 and offers a window into Connecticut’s early American past. The classic New England Town Green and the Prudence Crandall Museum stand out.
The Prudence Crandall Museum documents an extraordinary woman and her attempt to educate black women during a time of violent oppression. Prudence’s neighbors and friends ostracized her here and forced her to close her school and eventually move away from the area.
During the fall foliage season, Wright’s Mill Tree Farm offers a spooky hayride and the chance to pick your own pumpkin. This 250 acre farm is located on the north end of Canterbury.
Continue on Route 169 the 7 miles to Brooklyn, where on the way you will pass farms and houses nestled in the hills in this area of Connecticut known as the “quiet corner.”
Brooklyn is a history buffs dream. You will discover a large number of historic buildings with a high concentration of them in a 1.75 acre area known as Brooklyn Green. Both Brooklyn and Brooklyn Green are on the National Register of Historic Districts.
Places to see include the Friendship Valley Inn, a stop on the Underground Railroad, and where Prudence Crandall took refuge during her tour, and the old 18th-century Brooklyn Cemetery. The nearby C. Vaughan Ferguson, Jr. Conservancy offers walking trails through swamps and hills.
The best way to visit Brooklyn Green is to simply park your car and walk through it. With five churches on the green and a cluster of historic buildings, statues and memorial stones, something will catch your eye to explore further.
Leaving Brooklyn on Route 169 and heading north toward Pomfret, you’ll pass the 200-acre Lapsley Orchards orchards in the Bush Hill Historic District. Here in the fall you can pick apples or buy the perfect pumpkin for your front porch.
Another alternative trip worth taking before reaching Pomfret is Mashamoquet Brook State Park and Putnam Wolf Den. At the junction with Route 101 head west and take the park entrance less than a mile down Route 101. With the abundance of maples and oaks in the park, the fall foliage is dazzling. Be sure to hit the trail and walk to Wolf Den, where a plaque describes the death of the last wolf in Connecticut.
Back on Route 169, travel the next few miles to downtown Pomfret.
A stroll through Pomfret presents another opportunity to see an 18th century cemetery in the Sabin cemetery, 19th century churches, and a 13th century French window in the Pomfret school chapel.
Head north on Route 169 from Pomfret towards Woodstock on the last leg of this scenic drive. Before arriving in the quaint New England town of Woodstock, you’ll have the opportunity to explore more hiking trails at The Connecticut Audobon-Pomfret Farms and The Air Line Trail.
Once in Woodstock, head to Roseland Cottage, a striking pink Gothic Revival house that is also home to the Bowen Museum. The home has original furnishings and tours are offered from June to October.
Woodstock has a classic New England town vibe, with a village green lined by Maples and an old cemetery, meeting house, and many 18th century houses on the perimeter.
And if you’d rather not return to home base but rather relax in Woodstock for the night, the Inn at Woodstock Hill has suites and rooms with fireplaces. The inn is on the National Register of Historic Places and is a fitting end to this scenic drive in Northeast Connecticut.
Traveling Connecticut’s Route 169 is a perfect New England jaunt any time of year, but especially during the fall foliage, when the scent of fall fills the country farms and towns along the route.