Hiking Trails & Parks in Chestertown, Maryland
3 hiking & walking trails and 0parks, recreation areas & campgrounds in Chestertown, located in Kent County, Maryland. Free trail map for every listing.
About Outdoor Recreation in Chestertown, Maryland
Chestertown offers 3 mapped hiking trails and 0 federally managed parks within the city or nearby. Located in Kent County, Maryland, it’s a starting point for hikers, campers, and casual nature seekers.
Explore more nearby: Kent County overview, all Kent County trails, or statewide Maryland list.
Hiking Trails in Chestertown
Curated Guides for Chestertown
Frequently Asked Questions
Are there hiking trails in Chestertown, Kent County, Maryland?
Yes — we have 3 mapped hiking and walking trails in Chestertown, Kent County, Maryland, sourced from OpenStreetMap. Browse the full list below, with distance, elevation, and difficulty for each.
What is the best hiking trail in Chestertown, Kent County, Maryland for families?
Wayne Gilchrest Trail near Chestertown is one of the best family picks in Chestertown, Kent County, Maryland — 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 Chestertown, Kent County, Maryland?
Each of the 3 trails in Chestertown, Kent County, Maryland 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 Chestertown, Kent County, Maryland?
We don't have parks or recreation areas mapped in Chestertown, Kent County, Maryland yet.
Can I go camping in Chestertown, Kent County, Maryland?
We don't show any campgrounds with mapped campsites in Chestertown, Kent County, Maryland right now — check the county level for more camping options nearby.
Where can I find hiking trails and parks near Chestertown, Kent County, Maryland?
Browse all hiking trails, walking trails, parks, and campgrounds across Kent County for more options beyond Chestertown, Kent County, Maryland.
From the OutsideAtlas Blog
Photo: Tobias MrzykThe 10 Longest Hiking Trails in Maryland, Ranked
Maryland's longest mapped hiking trails, ranked by distance with notes on what makes each route worth the commitment.
Photo: Tobias MrzykMaryland's 10 Most Punishing Trails by Elevation Gain
Steep is hard. These are the ten Maryland trails with the most total elevation gain — quad-burners earned by hard climbing.
Photo: Maddi BazzoccoThe Best Beginner-Friendly Hikes in Maryland
Ten gentle, well-marked Maryland trails perfect for first-time hikers, families, or recovery days.
Photo: Tobias MrzykThe 10 Most Challenging Hikes in Maryland
Maryland's ten hardest hikes — expert difficulty, big mileage, or serious exposure. Reserved for experienced hikers.
Photo: Diego LozanoThe Best National Parks & Recreation Areas in Maryland
Federal parks and recreation areas in Maryland ranked by what they actually offer hikers and campers, not just popularity.
Photo: Tobias MrzykBest Waterfall Hikes in Maryland: 10 Trails to See Falls Up Close
Maryland's best hikes to named waterfalls — from short family-friendly viewpoints to all-day cascade chasing.