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Fall Foliage Scenic Drive in Connecticut

Fall foliage scenic drives in Connecticut include the Long Island Sound coastal routes, and the Litchfield Hills in Northwestern Connecticut. These areas offer dramatic scenic drives any season, but for me, the trip that comes alive in the fall is nestled in eastern Connecticut’s “Quiet Corner” and is Route 169. This is a gem of a fall foliage scenic drive in Connecticut. Let me take you for a quick spin…

Fall Foliage Scenic Drive in ConnecticutPeak fall foliage in Connecticut usually starts mid-October and lasts through end of October, sometimes drifting into early November. Connecticut has a milder climate than many other areas of New England, as evidence by the plethora of wineries and vineyards enjoyed by the region these days. Many scenic routes take you close to one of the 16 open for visiting.

But back to our fall foliage route…

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 opportunities to soak up the color and take an eye-popping memory snap. The drive follows Route 169 from Lisbon, CT, to the border with Massachusetts. Though it’s just a short drive of over 30 miles, nonetheless as you’ll see it packs a lot into a small area.

Begin your scenic drive in the town of Lisbon, which can be reached, from I-395 exit 83A. The center of town is known as Newent. In the town visit the Bishop House Museum and the Newent Congregational Church for a flavor of some of the architectural styles in this region of Connecticut.

Follow 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.

Prudence was an extraordinary woman, and The Prudence Crandall Museum documents her attempt to provide education for black women during a time of violent oppression. Prudence’s neighbors and friends eventually ostracized here and forced her to close her school and move away from the area never to return.

Wright’s Mill Tree Farm is a pick-your-own local favorite, and during the fall foliage season offers a spooky hayride, and the chance to pick-your-own pumpkin.  This 250-acre farm is in the north end of Canterbury.

Travel the 7 miles to Brooklyn, where along the way you’ll pass farms and homes set among the rolling hills and fields of the region. Brooklyn is steeped in history.  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 trial, and the 18th century Old Brooklyn Burying Ground. The close-by C. Vaughan Ferguson, Jr. Conservancy offers walking trails among marshlands and hills.

The easiest way of visiting Brooklyn Green is simply to park the car and walk. 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 crisp 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 events leading to 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. Pomfret is also home to Sharpe Hill Vineyard, one of the wineries on the Connecticut Wine Trail, and open for touring and wine-tasting.

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

Connecticut is deep in museums and historic homes, and in Woodstock it comes together at 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 where you started but relax in Woodstock for the evening, then the Inn at Woodstock Hill have 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 eastern Connecticut.

As you travel along Route 169 keep your eyes open for the antique and bargain shops in the towns and villages. Connecticut is the antique “capital” of New England and with the right browsing you’re bound to discover that perfect treasure for your home.

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.

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