During the fall, Connecticut's tree-lined highways and winding country roads provide a backdrop of dazzling colors to the perfect autumnal road trip. In addition to peeping the leaves, you can also enjoy the many small towns that offer visitors antique shopping, wine tasting, and many brunch-worthy restaurants. Connecticut is a relatively small state, so there are a lot of ways to navigate a route for yourself using some of these roads and landmarks as your guide.
Connecticut Wine Trail
Autumn is the perfect time to explore wineries, and Connecticut has some of New England's finest. Allow the leaves to light your way, as you meander from vineyard to vineyard for tastings, tours, music, and special events. Be sure to have your Passport to Connecticut Farm Wineries stamped at each stop for your chance to win travel, wine, and other prizes. Some notable vineyards and wineries worth stopping for include: Lost Acres Vineyard, Arrigoni Winery, and Sharpe Hill Vineyard.
If you have one to two days, this tour explores the Lower Connecticut River Valley. You'll begin in Hamburg Cove and then travel north on Route 156, Route 82, and Route 434 up to the Devil's Hopyard State Park, where you'll find a lovely natural waterfall. After crossing the river on Route 82, stop in East Haddam to see the Gillette Castle and Godspeed Opera House. Afterward, continue south and consider grabbing lunch in Chester, a laid back town, where you can even take a ferry ride. After all that driving, you can finish up the trip at the Connecticut River Museum, where you'll learn more about this historic body of water.
Designated a National Scenic Byway, Connecticut's Route 169 is a historic roadway that will take you to museums, cute shops, and nearly 200 historic structures built before 1855. All of this is set in a scene of beautiful fall foliage. This 32-mile trip takes about an hour to drive without stopping, so it can easily be done in a day or two, depending on how many colonial homesteads and churches you want to stop for.
There's something so romantic about stumbling upon a covered bridge nestled within a picture-perfect fall landscape. If you don't want to leave finding a "kissing bridge" to chance, you'll find a good amount of them in the western part of the state. Begin your journey by crossing Bulls Bridge and visiting Kent Falls State Park, where you can hike to a wide waterfall and cross a pedestrian-only covered bridge. Next, you can take Route 128 east do drive across the West Cornwall Bridge and then head south on Route 63 to Lake Waramaug.
The Merritt Parkway, Connecticut Route 15, winds through Fairfield County, and while it's a prime commuters' route Monday through Friday, it provides incredible scenic driving on the weekends. It has been designated a National Scenic Byway and in addition to the fall foliage that lines this route, you'll also ride along some bridges that are good examples of the Art Deco and Art Moderne style of the 1920s and 1930s. If you care for fishing, the Hemlock Reservoir is an on-the-way place to hop off the highway and cast a line while enjoying the reflection of autumn colors in the water.
The penalties are steep: Here's what you need to know before you hit the road this fall.