Hiking Trails in Connecticut & Massachusetts
Hiking Trail Map – Northwest Connecticut and Litchfield Hills
From easy and family-friendly – to challenging and super-rewarding – this region of Connecticut and Massachusetts offers dozens of hiking trails for all abilities. We’ve linked to the best available hiking trail maps available, and hope that you will enjoy!
Click the map icon (or here) for the Northwest Connecticut and the Litchfield Hills Hiking Trails Map. This map is courtesy of the Northwest Hills Council of Governments and Housatonic Valley Association.
Hiking Trails in Western Massachusetts and Berkshire County
Visit the Berkshire Natural Resources Council for the Top Berkshire Trails!
Blue-Blazed Hiking Trails Interactive Map
Visit the CFPA’s interactive map: Blue-Blazed Hiking Trail System!
Use this interactive map to enhance your hike planning.
- Click on the trail lines to learn trail names and length.
- Select the Show Parking option in the top right corner to see trailhead parking locations.
- Use the Zoom and Street View (person icon) tools on the bottom right to see more area details.
- Click on specific parking locations (P icons) to view more details and link to driving directions.
For detailed descriptions of any major trail interruptions or closures that may affect your hike, click on the CFPA Trail Notices Page.
Whenever you’re planning to hit the trails, the latest information is waiting at the CFPA’s website for you. Have a fun and safe journey!
Hiking & Walking Trail Links
Here are additional resources for hiking and walking trails in Berkshire County and Litchfield County.
We encourage you to practice good personal safety measures (along with the usual trail etiquette and whatever other rules may apply at these individual locations), and visit these amazing trails that are generally accessible to the public during daylight hours:
Connecticut Trails & Organizations:
- Cornwall, Kent, Warren-CT: Wyantenock State Forest
- Cornwall, CT: Cheryl Cadman Evans Preserve
- Falls Village, CT: The Nature Conservancy–Hollenbeck Preserve
- Kent, CT & New Milford, CT: Northwest Connecticut Land Conservancy/Weantinoge–10 nature preserves
- Kent, CT: Kent Land Trust–9 nature preserves in Kent
- Kent, CT: Pond Mountain Trust Natural Area
- Kent, CT: Kent Falls State Forest
- Kent, CT: Lake Waramaug State Forest
- Kent, CT: Macedonia Brook State Forest
- Kent, CT: The Nature Conservancy–Iron Mt. Preserve
- Norfolk, CT: Norfolk Land Trust–8 nature preserves in Norfolk
- Norfolk & Falls Village, CT: Great Mountain Forest
- Norfolk, CT: Campbell Falls State Park
- Norfolk, CT: Dennis Hill State Park
- Norfolk, CT: Haystack Mt. State Park
- North Canaan, CT: Beckley Iron Furnace State Park
- North Canaan, CT: Iron Trail
- Salisbury & Lakeville, CT: Numerous hiking trails in the Salisbury/Lakeville area
- Salisbury/Lime Rock, CT: Salisbury Land Trust–Sycamore Field Preserve
- Salisbury, CT: Railroad Ramble
- Salisbury, CT: Mt. Riga State Park
- Sharon, CT: Housatonic Meadows State Forest
- Sharon, CT: Sharon Land Trust Nature Preserves–10 nature preserves
- Warren, CT: Warren Land Trust Nature Preserves–4 nature preserves
- Washington Depot, CT: Steep Rock Association Preserves–3 nature preserves
- Washington, CT: Steep Rock Association Preserves–Holiday House Trail
- Kent, Sharon, Canaan, Salisbury: Appalachian Trail in CT–52 miles of trail
Massachusetts Trails & Organizations:
- Alford, MA: Berkshire Natural Resources Council–Alford Springs
- Chester / Becket, MA: Keystone Arches Bridge Trail
- Becket, MA: Becket Land Trust–historic quarry & trails
- Great Barrington, MA: Great Barrington Land Conservancy Nature Preserves
- Great Barrington, MA: Berkshire Natural Resources Council–Housatonic Flats
- Great Barrington, MA: Berkshire Natural Resources Council–3 Mile Hill
- Great Barrington, MA: Berkshire Natural Resources Council–Thomas & Palmer Brook Preserve
- Hinsdale/Dalton, MA: Berkshire Natural Resources Council–Old Mill Trail
- Lanesborough, MA: MASS DCR-Ashuwillticook Rail Trail
- Lanesborough, MA: MASS DCR–Mt. Greylock State Forest
- Lanesborough, MA: Berkshire Natural Resources Council–Constitution Hill
- Lee, MA: MASS DCR–October Mt. State Forest
- Lee, MA: Berkshire Natural Resources Council–Basin Pond
- Lenox, MA: Edith Wharton’s ‘The Mount’
- Lenox, MA: Mass Audubon–Pleasant Valley Sanctuary
- Lenox, MA: Berkshire Natural Resources Council–Yokun Ridge Reserve
- Lenox, MA: Berkshire Natural Resources Council–Parsons Marsh
- Monterey, MA: Monterey Preservation Land Trust–Mt. Hunger
- Monterey, MA: Bidwell House Museum trails
- Monterey, MA: MASS DCR–Beartown State Forest
- Monterey, MA: Berkshire Natural Resources Council–Bob’s Way
- Monterey, MA: Berkshire Natural Resources Council–Steadman Pond at Hudson Howard
- Mt. Washington, MA: MASS DCR–Mt. Washington State Forest
- New Marlborough, MA: New Marlborough Land Trust–Joffe Nature Sanctuary
- New Marlborough, MA: New Marlborough Land Trust–New Marlborough Preserve
- New Marlborough, MA: New Marlborough Land Trust–Lower Carroll Mill
- New Marlborough, MA: New Marlborough Land Trust–Goodnow Preserve
- New Marlborough, MA: New Marlborough Land Trust–1000 Acre Swamp
- New Marlborough, MA: The Trustees of Reservations–Dry Hill Reservation
- New Marlborough, MA: The Trustees of Reservations-Questing Reservation
- New Marlborough, MA: Berkshire Natural Resources Council–Steepletop
- Pittsfield, MA: Hancock Shaker Village–hiking trails
- Pittsfield, MA: Mass Audubon–Canoe Meadows Wildlife Sanctuary
- Pittsfield, MA: MASS DCR–Pittsfield State Forest
- Pittsfield, MA: Berkshire Natural Resources Council–The Boulders
- Richmond, MA: Berkshire Natural Resources Council–Hollow Fields
- Sandisfield, MA: Berkshire Natural Resources Council–Clam River
- Sheffield, MA: Mass Audubon–Lime Kiln Farm Wildlife Sanctuary
- Sheffield, MA: The Trustees of Reservations–Bartholowmew’s Cobble
- Sheffield, MA: Sheffield Land Trust–Schneck Property
- Sheffield, MA: The Nature Conservancy–Drury Preserve
- Stockbridge, MA: Stocbridge Bowl Assoc.–Bullard Woods
- Stockbridge, MA: Laurel Hill Assoc.–Ice Glen Trail, Laura’s Tower Trail, Mary Flynn Trail
- Stockbridge, MA: Berkshire Natural Resources Council–Jackson Pond
- Stockbridge, MA: The Trustees of Reservations–Monument Mountain Reservation
- Tyringham, MA: The Trustees of Reservations–McClennan Reservation
- Tyringham, MA: The Trustees of Reservations–Tyringham Cobble Reservation
- West Stockbridge, MA: Berkshire Natural Resources Council–Stevens Glen
- Windsor, MA: Tamarack Hollow Nature & Cultural Center
- from CT border to VT border: Appalachian Trail in MA–90 miles of trail