The 16 Best Hiking Trails in Connecticut!

Connecticut, the fourth most populated state in the country, is one of the most beautiful places in the entire New England region, known for its brilliant fall foliage, breathtaking New England shorelines, and picturesque farmland. You won’t have to wait for the perfect fall season to take advantage of its spectacular hiking trails, and you can do some good while you’re out there as well. Whether you’re seeking the best scenic trails to enjoy or you’re looking for excellent places to hike or run, here is our definitive list of the 16 best hiking trails in Connecticut.

1. Maple Ridge Trail

Maple Ridge Trail is located within the Mohawk Trail State Park in Guilford. Known for its beautiful views of Long Island Sound and Long Island, the trail is a part of the 3,744-mile Long Trail, which extends from Woodstock, Vermont to Dover, New Hampshire. Originally built for maintenance workers to traverse the long-range trail, the Maple Ridge Trail offers approximately five miles of moderately difficult trail that pass some of the most amazing Long Island Sound shoreline vistas in Connecticut. At the end of the trail, you’ll be treated to a final view of the bustling Long Island Sound before heading back the way you came.

2. Castle Hill

Castle Hill State Park is a state park located in Norwalk, Connecticut, just a few miles from the famed Trump National Golf Club in Westchester, NY. This forested trail is 6.1 miles long and is one of the state’s most popular. Along this undulating terrain, you’ll pass the historic Cos Cob Airstrip, the site of a World War II anti-aircraft battery. It is a little muddy in parts and visitors should be careful not to slip. The short trail ends at the Cos Cob overlook, which offers panoramic views of both the New York Harbor and the Long Island Sound.

3. Witch Hill Trail

Witch Hill Trail is a 4.7-mile-long narrow greenway that crosses through the Puritan Hollow Park in East Granby. It offers dramatic views of the Quinebaug River. The route passes through a ravine on both sides, a distinctive landscape that can be found in the Town of New Hartford and other parts of northern Connecticut. It is the most used trail in the park, which is designed for horseback riding and mountain biking. The Park and Trail is the place where the New England Emigrant Trail used to pass.

4. Quinebaug Ridge Trail

The Quinebaug Ridge Trail is a historic hiking and bicycling trail that traces the Quinebaug River. On the trail, you’ll see the remains of an aqueduct, three dams, old railroad bridges, and forests of old-growth pine and birch trees. Located within the Quinebaug Valley State Park, the trail is about 10 miles long. It connects to the Hilltop Trail, the Cheshire Trail, the Ripton Falls Trail, and the Indian Falls Trail. It is best to start at any of these trails, and then hike or bike to the Quinebaug Ridge Trail. It’s best to check the New England Environmental Agency trail map, which includes directions on how to get to the trail, and the best route to follow.

5. Washington’s Crossing Trail

Washington’s Crossing Trail is an off-trail hiking trail located within the Plains and Parks Trail. The trail’s mile and half loop are complete with a stone aqueduct bridge, stone arches, and a scenic spring. In early summer, the trail is very popular for frog hunting. While the trail is secluded, it is easily accessible and, like other trails in the New England Greenway, is perfect for walkers and bikers. It can also be used as a shortcut to the North Church in Washington. The walk is about 3.5 miles long.

6. Hanover Hill Trails

The Hanover Hill Trails is a series of trails that follow the hills of the town of Oxford, Connecticut, providing visitors with stunning views of the Connecticut River Valley. The trails are around 2.5 miles long and offer hikers, runners, and bikers a rewarding route around the town. In the summer, it is not uncommon for users to take the trail to the town of Stockbridge, Massachusetts, and explore Oxford’s historic shops and architecture.

7. John Stark Nature Trail

The John Stark Trail is a 5.8-mile-long trail located on 117 acres of what was once the Thorne Farm and carriage house. The trail is part of the Chardin Trail, which runs from the Prosser Reserve to Southwick Farm, and offers stunning views of the Guilford Reservoir. Hikers can also take advantage of the trails to explore Thorne Nature Center and its nature trails.

8. Sacred Valley Greenway

The Sacred Valley Greenway is a 3.2-mile-long off-road recreational trail in the Northwest Hills of Torrington, Connecticut. It’s popular with nature lovers and cyclists. It’s a great place to see wildlife such as ducks, red squirrels, rabbits, turtles, and foxes. Visitors can also use the greenway for off-road biking and hiking. The hike can last from 30 minutes to three hours.

9. Olmsted Trail

The Olmsted Trail is a hiking and biking trail that meanders through Glen Helen in Westport, Connecticut. It’s a scenic trail that features the river and a flowing stream. It offers stunning views of the Connecticut River and the two dozen-plus rock outcrops that overlook the river and town. It’s a popular trail that offers a scenic hike and great access to Connecticut River waterfront trail and park.

10. Landscape Farm Trails

The Landscape Farm Trails is a 6.1-mile trail in Stafford Springs, Connecticut. It’s perfect for visitors who want a leisurely hike in the countryside. It follows the Connecticut River to River Road, which is a popular biking and walking route that follows the river. The trail is located within Landscape Farm, preservation of historic farmland. The trail is easy to follow and has easy access to restrooms and parking. The trail offers a great scenic hike through fields and farmlands.

11. East River Greenway

The East River Greenway (bit.ly/2dAYu4w) is off-road biking and walking trail that runs from Treadwell Park in Vernon, Connecticut to the Town Green in Hartford. The trail provides two separate routes. One route runs along the banks of the Housatonic River, while the other route follows the Town Green, crossing into downtown Hartford via the Connecticut Riverwalk, with views of the Connecticut State Capitol. The East River Greenway is a great way to see what the downtown Hartford area has to offer.

12. Garden Trail

The Garden Trail is an off-road biking and hiking trail located in Shelton, Connecticut. It’s a beautiful 2.5-mile loop that follows along the Guilford and Woodbridge Rivers. The trail includes tree-lined trails and scenic views of ponds, nature preserves, and downtown Shelton. It’s a great place to spend an afternoon or evening.

13. Farmington Greenway

The Farmington Greenway Trail is a 3.2-mile hiking and biking trail that takes visitors to historic and culturally significant areas of Farmington, Connecticut. The trail takes visitors to Shelton Falls Preserve, Farmington Canal Greenway Trail, Mount Auburn Cemetery, and the Orchard Hill Country Club. The trail runs along the Farmington Canal Greenway Trail, which is a beautiful elevated trail that runs from Farmington to New Haven.

14. Missisquoi Valley Trail

The Missisquoi Valley Trail is a 1.5-mile trail in Vergennes, Vermont. It provides a scenic walk along the Missisquoi River. The trail is on the National Trail System and is one of the shortest and easiest trails to follow in the state. It’s a great place to view wildlife such as eagles, mallards, and waterfowl. The trail is paved and fairly flat and has good access to restrooms and parking. It’s a good option for beginners who want to experience a short and easy walk-through of nature. Visitors can also enjoy views of the Champlain Bridge and downtown Vergennes.

15. Ellen Browning Scripps Park Trail

The Ellen Browning Scripps Park Trail is a 5.8-mile trail in Orange, Connecticut. The trail is wheelchair accessible and goes along the banks of the Mill River and through many different nature preserves. The trail has lots of great scenic views and also has a paved trail surface and parking. The trail can be difficult to follow but is also relatively flat. Visitors can either walk the trail or bike the trail. The trail is very scenic and should not be missed.

16. Thimble Shoals State Park Trail

The Thimble Shoals State Park Trail is a 2.7-mile trail in Milford, Connecticut. It provides a scenic, mostly flat, and paved jogging and cycling trail. It has easy access to bathrooms and parking and is an easy option for newbies. The trail runs through wooded preserves and along the Milford waterfront. It’s a great option for people who want to spend an afternoon out on the water. Visitors can also enjoy views of downtown Milford, as it looks out across the water toward Long Island Sound.

17. Berkshire Greenway

The Berkshire Greenway is a 2.3-mile trail in Lane’s borough, Massachusetts. It provides a short but scenic hike through the Berkshire Hills of Western Massachusetts. It’s a great destination for hikers, cyclists, and runners. It’s an easy and pleasant trail for newbies, as it follows the Riverton Greenway Trail. It’s a well-maintained path that follows along the banks of the Riverton River. It has many great overlooks and has many beautiful scenic vistas. It’s a great place to see fall foliage or just enjoy nature.

18. Great Western Trail

The Great Western Trail is a trail that travels along with the New York, New Jersey, and Connecticut borders. It has a total length of 27.5 miles. It passes through four states and is designated as a trail for walking, hiking, and cycling. It’s one of the most scenic trails in the state, with beautiful views and good access to camping and other amenities along the trail. It’s a great place to spend an afternoon, and a great way to experience the beauty of Connecticut.

19. Haddam Neck State Park

The Haddam Neck State Park Trail is a 4.3-mile trail that winds along the Haddam Neck State Park Trail. The trail provides visitors with views of the Connecticut River and the Haddam Neck Wildlife Refuge. The trail also provides access to bathrooms and parking. It’s a fairly flat trail that passes through mixed forest. It’s a good option for those who want to spend the day exploring nature. It’s also a good option for hikers and mountain bikers who want to check out the national recreation trail.

20. Chittenden Reservoir State Park Trail

The Chittenden Reservoir State Park Trail is a 9-mile trail that travels through the Westchester, Putnam, and Middlesex counties of Connecticut. It is wheelchair accessible and provides wonderful views of the lake and the area surrounding the lake. The trail passes through a nature preserve, and passes through many state parks and forests, providing visitors with plenty of sights to see. The trail also passes near many small villages that have an interesting history. It is a popular trail and a great one for bicyclists and hikers who want to explore New England.

21. Shepaug River Greenway

The Shepaug River Greenway is a 3.8-mile trail that begins at 8 Frontage Road, South Glastonbury, Connecticut. It travels along the Shepaug River, providing scenic views of the Glastonbury Reservoir and Mount Carmel. It has easy access to parking and provides a great route to check out the river. The trail is wheelchair accessible and is great for people who want to get out and experience nature. It’s a great trail for those who want to spend the day and enjoy the gorgeous views.

22. Beacon Hill Greenway

The Beacon Hill Greenway Trail is a 4.1-mile off-road bike and hiking trail that’s one of the most scenic trails in the state of Connecticut. The trail runs along the steep hillsides of Beacon Hill in Hartford, Connecticut. It is wheelchair accessible and is a great way to see the state capital. It passes through several parks and historic landmarks and offers visitors views of the Hartford skyline, as well as the First Congregational Church and Park.

Conclusion

Connecticut is filled with a wide variety of trails, and each has its unique features. Some are not wheelchair accessible or allow bicycles. The state is also known for its many lakes and offers opportunities for swimming. Make sure you explore the trails before you go, and check out the different parts of the state. You may even get a chance to meet some locals, and hear about the history of Connecticut. Did we miss any great trails in the state? If so, be sure to share them with us in the comments!