8 Great Road Trips to Take in Connecticut
Nothing beats a road trip through New England, regardless of the time of year. In the winter, hit the slopes; in spring, enjoy wildflowers; in summer, head to the beaches; and in the fall, the changing colors and crisp air will have you glued to the window as the storybook scenery unravels. Connecticut, with its charming towns, picturesque landscapes, and rich history, offers a plethora of scenic routes perfect for exploring the beauty of the season. From the rolling hills of Litchfield County to the coastal towns along Long Island Sound, each drive reveals a different side of the state.
Along the way, they reveal hidden historical landmarks, cultural sites, and tiny towns, where every turn offers stunning views and memorable experiences. So, grab your map, pack your snacks, and get ready for an unforgettable adventure through the heartland of the Nutmeg State!
Lisbon To Woodstock
The trip from Lisbon to Woodstock takes about 40 minutes, straddling the iconic Route 169. It takes you through some of Connecticut's most spellbinding vistas, exposing classic New England wooded landscape. Several worthwhile stops along the pathway call on road trippers to stop and admire local attractions. In Canterbury, you can choose from several museums to explore local heritage. These include the Prudence Crandall Museum, which preserves the first African American school for girls.
Besides the beautiful nature, visitors have an opportunity to encounter native wildlife species in Brooklyn with a trip to Creamery Brook Bison. As you approach Pomfret, prepare to immerse in the great outdoors at Mashamoquet Brook State Park. This beautiful sanctuary also offers opportunities for fishing, camping, and hiking.
Greenwich To Orange
For about 45 minutes, this exciting road trip goes on a rollercoaster of experiences, featuring everything from beautiful nature and historical landmarks to vibrant arts. Brace yourself for the numerous stops to come, starting with the Stamford Museum and Nature Center. While there is no shortage of things to see and do in Norwalk, the Maritime Aquarium at Norwalk is a must-visit. The remarkable facility offers a taste of the underwater life in nearby Long Island Sound by exhibiting over 300 maritime species.
Later, in Bridgeport, find inspiration through rare interactions with exotic land animals with over 100 species at Connecticut's Beardsley Zoo. Alternatively, catch a riveting performance on stage at the Downtown Cabaret Theatre by talented artists.
Brookfield To Litchfield
This exciting trip through the heart of Connecticut lasts less than an hour but features plenty of attractions that significantly lengthen the trip. New Milford is the first major stop on the journey, welcoming tourists to explore its many nature spaces. Take a break to enjoy a hike in Lovers Leap State Park, which has beautiful scenery with unprecedented vistas of the Housatonic River and Lake Lillinonah. Meanwhile, appreciate the culture at the Village Center for the Arts, featuring exhibitions and performances.
There is more beautiful nature to experience when you reach Washington, home to the Hidden Valley Preserve. Almost 20 miles of trails traverse this 940-acre network of woodlands. Before resuming the drive, make sure you have a full stomach by popping into the Po Cafe.
Kent To Canaan
You only need 30 minutes to complete this trip, but there are numerous stops to anticipate along the way. A few minutes into the trip, you will come across Kent Falls State Park, a nature lover's playground with a picturesque series of waterfalls. Prepare for more adventures in the outdoors at Housatonic Meadows State Park. This adorable 450-acre sanctuary beckons enthusiasts with a range of opportunities, from fishing and canoeing to picnicking and hiking.
On your last stop, use the opportunity to restock with a delicious meal at the Caddie Shack. Finally, you can wrap up your itinerary at the Beckley Iron Furnace State Park, which houses a 19th-century furnace listed on the National Register of Historic Places.
Canton To Putnam
If you have enough time on your hands to discover Connecticut's rural communities, the one-hour journey between Canton and Putnam will take you through a treasure trove of beautiful towns. Highlights include Farmington, which harbors a range of attractions, but you can settle for an artsy adventure at Hill-Stead Museum. A short drive ahead in Manchester, the Shoppes at Buckland Hills allows you to purchase any supplies you might be missing, thanks to over 100 specialty stores.
Willington is another worthwhile pause, and its lively restaurant scene invites passers-by to enjoy a nice meal at Hilltop Restaurant Bar & Banquet. Finally, remember to take advantage of the lovely nature space at Natchaug State Forest, which offers everything from fishing and hiking to picnicking.
Orange To Stonington
Connecticut's picturesque coastline spoils drivers with unprecedented vistas of the Atlantic Ocean, making this one-hour drive one of the most scenic road trips to take in Connecticut. The route weaves through notable waterfront communities that let you admire the scenery and discover local points of interest. Guilford makes for an excellent first stop and transports guests back to the 18th century at the Hyland House. Alternatively, you can revel in the cozy sea breeze at Jacobs Beach. If you love the arts, be sure to take a break in Old Lyme and get a feel for its vibrant art scene by touring the Florence Griswold Museum.
Elsewhere, discover Connecticut's maritime heritage at the Custom House Maritime Museum, a top attraction in New London. But if you fancy a gentle sail on the calm Atlantic waters, get on the Block Island Express for a unique perspective of the town.
Shelton To Thomaston
Much of this 30-minute adventure plays out along Connecticut Route 8 and introduces vacationers to the state's inland natural beauty. Besides nature, it also passes underrated towns waiting to be discovered, beginning with Ansonia. Here, you can peek into local heritage by browsing artifacts at the Derby Historical Society. A short distance ahead, you will come across the Naugatuck State Forest, which embodies the allure of Connecticut's countryside. The serene setting is perfect for a brief pause to commune with Mother Nature.
Waterbury is a must-stop, especially if you have an affinity for the arts. The vibrant city is awash with performance centers, inviting visitors to enjoy an entertaining concert at the Palace Theater. Before leaving, ensure you grab a delicious exotic meal at La Cazuela to set yourself up for the rest of the journey.
Old Saybrook To Haddam
This beautiful route straddles the Connecticut River Valley, so bring a camera to document the majesty of the stunning waterway as it cascades through the state's rural communities. Expect to come across historic lighthouses, marinas, and vistas along the river course. One of the first places to check out is Essex, which invites you to learn interesting facts about the river at the Connecticut River Museum. Further along, the tiny village of Deep River offers a taste of the region's thriving craft beer scene at High Nine Brewing.
But before starting to indulge in the great-tasting brews, pass by the Red House to make sure your stomach is full. Finally, stop in in Chester to enjoy a family-friendly musical at the Terris Theatre if you can spare the time.
Embarking on a road trip through Connecticut offers a delightful way to experience the state’s natural beauty, rich history, and charming communities. From the vibrant fall foliage to the picturesque coastal views, each journey unveils stunning landscapes and hidden gems that make the drive worthwhile. As you set out on these adventurous road trips in Connecticut, use the opportunity to stop, explore, and truly appreciate the local culture and attractions. Each road trip is a chance to connect with the beauty of New England and create lasting experiences with friends and family in the United States.
