Great Towns for Hiking Getaways Last Updated 11/19

Whether you are a seasoned hiker or enjoy more leisurely treks, the experience of going on a hike can benefit the mind and body. Connecticut offers hundreds of miles of hiking, biking and walking trails, including 52 miles of the Appalachian Trail. Perfect access points to these trails also happen to be nestled within some of the state's most charming towns. So to help you plan a richer adventure, here are a few suggestions for hiking getaways, including where to eat, stay and play.

Kent

From the rolling river with its historic covered Bull’s Bridge to Kent Falls State Park, the town of Kent offers endless natural beauty and a superb balance of quaint and chic offerings. Hiking trails can be found all over, including the famous Appalachian Trail, which runs through Kent following the Housatonic River—the longest riverfront stretch of the Appalachian Trail on the eastern seaboard. You’ll even run into one or two famous covered bridges while on the trail. The town receives hundreds of Appalachian Trail hikers yearly and features a welcome center that caters to hikers with a bathroom, hot shower, cell phone chargers, water bottle refilling station and a stainless-steel sculpture of a hiker at the entrance. Other great hikes in Kent include the Macedonia Ridge Trail, a challenging but exciting trek in Macedonia Brook State Park that provides stunning views of the Catskill and Taconic mountains. And then there’s the Pinnacle Trail, which overlooks Lake Waramaug—one of Connecticut’s most scenic bodies of water.

Make it a getaway: Stay and dine at the cozy Fife n’ Drum Restaurant & Inn, centrally located right on Kent’s main street and directly across from the town green. Downtown, you’ll find owner-operated shops offering stylish goods and antiques, including Main Street Antiques. Visit a beautiful cascading waterfall in Kent Falls State Park and then enjoy a variety of craft brews at Kent Falls Brewing Company, a farmhouse brewery with tours and tastings.

Simsbury

Just outside of Hartford, the town of Simsbury has the feel of a traditional New England town. You’ll find several trails in Simsbury, one of the most famous being the Metacomet Trail—part of Connecticut’s Blue Blazed Trail system—which runs through the entire length of the town. On this trail, visitors can enjoy an easy hike to Heublein Tower, a famous lookout tower in Talcott Mountain State Park. Or, follow the Metacomet Trail to Penwood State Park in Bloomfield, which features its own unique trail system of moderate to difficult hikes worth exploring.

Make it a getaway: Spend the night at the New England country-style Simsbury Inn and dine at Millwright’s Restaurant and Tavern overlooking a sparkling pond and gushing waterfall. To cross more activities off your bucket list, plan stops at Rosedale Farms & VineyardsTulmeadow Farm Store and Ice Cream Shop and Flamig Farm.

Washington

Nestled in the foothills of the Berkshire Mountains, the town of Washington offers visitors a plethora of fun and friendly things to do no matter the season. Steep Rock Preserve offers hiking trails that follow the banks of the Shepaug River. At the summit, visitors will encounter breathtaking views of the Clam Shell section of the Shepaug River Valley. There’s also the Hidden Valley Preserve, 700 acres of mixed forest and meadows with nearly 17 miles of hiking trails. Hikers will come across beautiful paths, meadows that are great for picnicking and the Henry David Thoreau Bridge, a suspension bridge featuring inscribed quotes throughout.

Make it a getaway: Stay at The Windemere B&B, just a two-minute drive from the center of Washington Depot, and dine at the White Horse Country Pub. Discover the diverse traditions, vitality and knowledge of Native American cultures at the Institute for American Indian Studies, and go for a tasting to sample award-winning wines at Hopkins Vineyard in New Preston.

Fairfield

The quaint coastal town of Fairfield is dotted with beaches, restaurants and unique experiences. It’s a great destination for a variety of beautiful hiking options. This includes the popular Lake Mohegan Loop, a moderate hike that features breathtaking views of Lake Mohegan and a waterfall along the way. Explore the Roy and Margot Larsen Wildlife Sanctuary, a 155-acre parcel composed predominantly of woodland, but interspersed with ponds and streams, meadows and emergent wetlands. It features over seven miles of trails and is a prime birding area, especially during the spring and fall migration. Or venture out to Lucius Pond Ordway/Devil's Den Preserve in nearby Weston, the Nature Conservancy’s largest preserve in that state that encompasses nearly 1,750 acres of land. This preserve features a 20-mile trail system with moderate to difficult pathways that lead to streams, wetlands, rock ledges, cliffs and more. 

Make it a getaway: Stay at the Circle Hotel in Fairfield, a charming southern New England boutique hotel, or the Hotel Hi-Ho, which offers a special leaf peeping getaway package in the fall. Wine and dine at the popular Barcelona Wine Bar. Also, visit the Connecticut Audubon Society Birdcraft Museum & Sanctuary and explore the past at the Fairfield Museum & History Center.

Woodstock

The town of Woodstock is packed with New England charm and history. It remains true to its agricultural roots, with pastoral scenery more dairy farms in operation than any other town in Connecticut. Its tranquil location makes it an ideal place to escape to nature. You’ll find great trails for leisure hikes in Bulls Hill Preserve, an unbroken forest that runs along the Woodstock and Thompson line.  And there’s Crystal Pond Park, featuring a beautiful lake, scenic hiking trails and a new disc golf course. Or for something a bit more challenging, head to nearby Pomfret, where you’ll find the Mashamoquet Brook Trail. This moderate loop within Mashamoquet Brook State Park takes you through wooded areas with opportunities to see various wildlife, birds, streams and other natural wonders—plus rewarding views at the summit. 

Make it a getaway: Stay at The Inn at Woodstock Hill, a restored country estate with an onsite restaurant. Visit Taylor Brooke Winery to taste and relax amongst the vines and then head over to its neighboring brewery to sample craft beer. Tour and explore the famous Roseland Cottage, a remarkably well-preserved example of Gothic Revival architecture featuring elaborate gardens

Madison

This charming shoreline town features over 50 miles of hiking trails and saltwater treks. This includes Rockland Preserve, where you’ll find rocky hills, a tranquil pond, steep gray cliffs and lovely wooded areas along its easy to moderate trails. There’s also Salt Meadow Park, where you can hike within a 10-acre coastal forest that has also become a sanctuary for migratory birds. Or if you’re looking for something less active and more relaxing, Hammonasset Beach State Park features an easy 3.4 mile heavily trafficked trail that offers views of over 2 miles of beach.

Make it a getaway: The town of Madison is filled with plenty of great opportunities to extend your stay beyond hiking adventures. Book a room at the Madison Beach Hotel and enjoy the private beach, onsite dining options, fitness room/yoga studio and more. Grab a Connecticut-style lobster roll or a piping-hot bowl of clam chowder at Lenny & Joe’s Fish Tale. Stroll the quaint downtown area and visit the famous bookstore, R.J. Julia Booksellers. End your visit with a tour of the historic Deacon John Grave House.