This Connecticut Scenic Byway Is The Road Trip Of A Lifetime

When people think of iconic American road trips, their minds often jump to Route 66 or California’s Pacific Coast Highway. But tucked away in the northeastern corner of the country lies a hidden gem that rivals them all, Connecticut’s State Route 169. Stretching roughly 32 miles from Lisbon, near the Rhode Island border, up to Woodstock, near Massachusetts, Route 169 offers a drive through the Quiet Corner, a region known for its rolling hills, vibrant fall foliage, and a sense of peace that’s hard to find anywhere else.

This National Scenic Byway captures the essence of New England in just a couple of days. Though Route 169 can be driven in just a day, this Connecticut road trip is an ideal weekend escape, whether you're chasing fall leaves, hunting for antique treasures, or simply looking to slow down and enjoy small-town life. With well-preserved architecture, covered bridges, classic diners, and stunning countryside vistas, Route 169 is the ultimate road trip, conveniently condensed into a manageable and unforgettable journey. Take a couple of days to enjoy Connecticut’s Route 169 with this road trip itinerary.

What It's Like to Drive Connecticut's Quiet Corner

Driving Route 169 feels like entering a postcard. The road winds gently through farmland, forest, and charming villages. Unlike the high-speed chaos of highways, this route is meant to be enjoyed at a relaxed pace. You'll pass white steepled churches, old stone walls, maple-lined roads, and red barns that haven’t changed in decades. It’s especially magical in the fall, when the trees are red, orange, and gold. The drive is quiet and leisurely, with low traffic and well-maintained roads, perfect for cruising with the windows down and your favorite playlist or podcast. During the winter months, it is advisable to drive with caution and be mindful of road conditions; however, Route 169 remains open year-round.

What sets Route 169 apart is its unique balance of natural beauty and historical significance. You're not just driving through picturesque landscapes; you're also traveling through the preserved culture of New England. This two-day itinerary offers the perfect blend of nature, history, and local attractions along the way.

Day One Itinerary: Lisbon to Pomfret (Approx. 1 hour driving)

The journey starts in Lisbon, a small town where Route 169 officially begins just East of Norwich. Start your morning at the John Bishop House, a museum and educational center located along Route 169, where you can learn about the local area's history through interactive activities, such as open-fire hearth cooking classes. After an interactive morning of learning, hit the road and head north along Route 169.

First Stop: Canterbury (15 min drive) Your first real immersion into the Quiet Corner of Canterbury. With extensive farmland and a low population density, the town of Canterbury is quiet, yet it holds a rich history. While stopping by, visit the Prudence Crandall Museum, a National Historic Landmark due to the significance the former school held in the fight for the right to education for women of color. Crandall v. Connecticut contributed to two Supreme Court decisions that helped shape the 14th Amendment in the U.S. Constitution. Afterward, take in the farmland at Burgis Brook Alpacas. Enjoy a 60-minute tour of the local alpaca farm to learn more about raising and harvesting alpaca fleece.

Next Stop: Brooklyn (15 min drive) Not to be confused with the borough of NYC, this Brooklyn is home to beautiful rural roads, antique shops, and the Brooklyn Green Historic District, but if you’re hungry, you can get some East Coast pizza at the local Brooklyn Pizza. If you're craving something else, grab lunch at Hank’s Restaurant, a classic roadside eatery with homemade comfort food.

Final Stop for the Day: Pomfret (20 min drive) Check in to an inn or bed-and-breakfast like the Quiet Corner Inn, just off of Route 169. Spend your late afternoon exploring Mashamoquet Brook State Park, where you can hike and visit “Wolf Den”, the site of Putnam’s wolf-slaying legend. For a more outdoorsy experience, powered campsites are available in the state park at Wolf Den Campground. In the evening, enjoy a quiet dinner at a local farm-to-table restaurant like The Vanilla Bean Café.

Day Two Itinerary: Pomfret to Woodstock (Approx. 30 min driving)

First Stop: Pomfret Center & Pomfret School Grounds. Even if you're not a student, take time to walk the campus of Pomfret School, a 500-acre hilltop campus that offers a look back on the route taken to get there. Depending on the season, watch the local Pomfret sports teams in action, go Griffins! Afterward, visit the Sharpe Hill Vineyard for a late morning tasting; they open around noon on weekends.

Final Stop: Woodstock (15 min drive) Woodstock is the crown jewel of the Quiet Corner. Explore the Roseland Cottage, a stunning pink Gothic Revival house built in 1846 with lush gardens and period furnishings. Loos Center for the Arts brings live music to the quiet corner year-round. Check the schedule and try to catch a show. Wrap up your journey with a casual lunch at Sweet Evalina’s Stand, known for pizza and sandwiches, or head to The Inn at Woodstock Hill for a final, more elegant bite before heading home.

Tips & Tricks for the Road

Best Season to Drive: Without a doubt, fall is the best time to experience Route 169. From mid-September to late October, the foliage is at its peak, and the scenery is nothing short of spectacular. That said, spring offers lovely blooms and fewer crowds, while summer is lush and green.

Travel Light: Many of the best experiences along Route 169 involve walking through small towns or trails. Wear comfortable shoes and bring a light jacket as temperatures can shift quickly in the countryside.

Don’t Rush: Though the drive itself is short, give yourself two full days to enjoy it. The charm lies in stopping frequently and soaking in the atmosphere.

Gas Up Early: While there are gas stations in each town, they can be spread out. Better to be safe than sorry, especially if you're venturing off-route to explore or travelling in winter road conditions.

Why Route 169 Belongs on Your Map

Route 169 may only span a little over 30 miles, but what it lacks in length, it more than makes up for in beauty, history, and fun activities. Whether you're a New England local or a first-time visitor, this road delivers everything a perfect road trip should: stunning views and fun experiences. In an era of busy interstates and digital distractions, this scenic byway reminds us that sometimes the best trips are the simplest ones in quiet corners. So fill up your tank, roll down your windows, and take the road less traveled. Connecticut’s Route 169 is waiting.