Hiking Trails & Parks in Bennington, Massachusetts
66 hiking & walking trails and 1parks, recreation areas & campgrounds in Bennington, located in Bennington County, Massachusetts. Free trail map for every listing.
About Outdoor Recreation in Bennington, Massachusetts
Bennington offers 66 mapped hiking trails and 1 federally managed parks within the city or nearby. Located in Bennington County, Massachusetts, it’s a starting point for hikers, campers, and casual nature seekers.
Explore more nearby: Bennington County overview, all Bennington County trails, or statewide Massachusetts list.
Parks & Campgrounds in Bennington
Hiking Trails in Bennington
Curated Guides for Bennington
Frequently Asked Questions
Are there hiking trails in Bennington, Bennington County, Massachusetts?
Yes — we have 66 mapped hiking and walking trails in Bennington, Bennington County, Massachusetts, sourced from OpenStreetMap. Browse the full list below, with distance, elevation, and difficulty for each.
What is the best hiking trail in Bennington, Bennington County, Massachusetts for families?
Appalachian Trail;Long Trail near Bennington is one of the best family picks in Bennington, Bennington County, Massachusetts — easy difficulty, short enough for kids and first-timers. See the full family hiking guide below for more options.
Is there a trail map for Bennington, Bennington County, Massachusetts?
Each of the 66 trails in Bennington, Bennington County, Massachusetts has its own page with an interactive map, GPS coordinates, and a link to view it on OpenStreetMap — no app or account needed.
What parks and recreation areas are in Bennington, Bennington County, Massachusetts?
Bennington, Bennington County, Massachusetts has 1 parks, recreation areas, and federal facilities in our index. Each listing includes activities, photos where available, and directions.
Can I go camping in Bennington, Bennington County, Massachusetts?
We don't show any campgrounds with mapped campsites in Bennington, Bennington County, Massachusetts right now — check the county level for more camping options nearby.
Where can I find hiking trails and parks near Bennington, Bennington County, Massachusetts?
Browse all hiking trails, walking trails, parks, and campgrounds across Bennington County for more options beyond Bennington, Bennington County, Massachusetts.
From the OutsideAtlas Blog
Photo: Sergei AkulichThe 10 Longest Hiking Trails in Massachusetts, Ranked
Massachusetts's longest mapped hiking trails, ranked by distance with notes on what makes each route worth the commitment.
Photo: Tobias MrzykMassachusetts's 10 Most Punishing Trails by Elevation Gain
Steep is hard. These are the ten Massachusetts trails with the most total elevation gain — quad-burners earned by hard climbing.
Photo: Sergei AkulichThe Best Beginner-Friendly Hikes in Massachusetts
Ten gentle, well-marked Massachusetts trails perfect for first-time hikers, families, or recovery days.
Photo: Holly MandarichThe 10 Most Challenging Hikes in Massachusetts
Massachusetts's ten hardest hikes — expert difficulty, big mileage, or serious exposure. Reserved for experienced hikers.
Photo: Diego LozanoThe Best National Parks & Recreation Areas in Massachusetts
Federal parks and recreation areas in Massachusetts ranked by what they actually offer hikers and campers, not just popularity.
Photo: Tobias MrzykBest Waterfall Hikes in Massachusetts: 10 Trails to See Falls Up Close
Massachusetts's best hikes to named waterfalls — from short family-friendly viewpoints to all-day cascade chasing.