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Fall Foliage Scenic Drive – Connecticut Route 169

by Cliff Calderwood

This fall foliage scenic drive runs south to north in the eastern corner of Connecticut along Route 169. Peak fall foliage in Connecticut usually starts mid-October and lasts through end of October.

Traveling Route 169 is as much about historic buildings and communities with traditions, as about brilliant color changes - although you’ll be blessed with plenty of leaf-peeping opportunities as well.

The drive follows Route 169 from Lisbon, CT, to the border with Massachusetts - A short drive of just over 30 miles but as you’ll see it packs a lot into a small area.

Let’s turn the ignition and get moving…

You’ll begin this scenic drive in the town of Lisbon, which can be reached, from I-395 exit 83A. The center of town is known as Newent.

Visit the Bishop House Museum and the Newent Congregational Church for a flavor of some of the architectural styles you’ll get familiar with during this drive.

Take Route 169 out of Lisbon/Newent and drive the 8 miles to Canterbury.

Named for the cathedral city in Kent, England, Canterbury was originally settled in 1697, and offers a window into Connecticut’s early American past. Highlights are the classic New England Town Green and the Prudence Crandall Museum.

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 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 in the north end of Canterbury.

Continue on Route 169 the 7 miles to Brooklyn, where along the way you’ll pass farms and homes set among the rolling hills in this area of Connecticut known as the “Quiet Corner.”

Brooklyn is a history buffs dream. You’ll discover historical buildings galore with a high concentration of them in a 1.75-acre area known as Brooklyn Green. Both Brooklyn and Brooklyn Green is on the National Register of Historic Districts.

Places to view include Friendship Valley Inn, a stop on the Underground Railroad, and where Prudence Crandall was given refuge during her trail, and the 18th century Old Brooklyn Burying Ground. The close-by C. Vaughan Ferguson, Jr. Conservancy offers walking trails among marshlands and hills.

The best way of visiting Brooklyn Green is simply to park the car and walk though it. With five churches on the green and a cluster of historical buildings, statues, and commemorative stones, something is bound to catch your eye to explore further.

Leaving Brooklyn on Route 169 and heading north towards Pomfret, you’ll pass the 200-acre Lapsley Orchards in the Bush Hill historic district. Here during the fall you can pick apples or purchase the perfect pumpkin for your front porch.

Another side trip worth taking before you reach Pomfret is Mashamoquet Brook State Park and Putnam Wolf Den. At the junction with Route 101 head west and take the entrance into the park less than a mile down Route 101. With the abundance of maples and oaks in the park the fall foliage dazzles. Be sure to take the path and short walk to the Wolf Den where a plaque describes the killing of the last wolf in Connecticut.

Back on Route 169 take the next few miles into the center of Pomfret.

A walk through Pomfret presents another chance to check out an 18th century graveyard at The Sabin Cemetery, 19th century churches, and a 13th century French window at the Pomfret School chapel.

Head north on Route 169 out of Pomfret for Woodstock on the last leg of this scenic drive. Before reaching the picturesque New England village of Woodstock, you’ll have the chance to explore more hiking trails at The Connecticut Audobon-Pomfret Farms and The Air Line Trail.

Once in Woodstock head for Roseland Cottage - a striking pink Gothic Revival style house which is also home to the Bowen Museum. The house has original furnishings and tours are offered June – October.

Woodstock has a classic New England village feel to it, with a village green lined by Maples and an old burying ground, meeting house, and many 18th century homes on the perimeter.

And if you prefer not to head back to home base but relax in Woodstock for the evening then 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 tour in Northeast Connecticut.

Traveling on Connecticut’s Route 169 is a perfect New England ramble any season, but especially during fall foliage , when the scent of autumn fills the countryside farms and the villages along the route.

Look for other articles in this series of fall foliage scenic drives. Or if you can’t wait you can pick up a free report containing these and other New England scenic drives along with detailed route coverage and attractions at

Cliff Calderwood is a travel and web copywriter living in Massachusetts.

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