1
Rolling Road Park
Managed by Town of Chestertown
20 acres0.1 mi of trail
Dog rules not recorded
DirectionsTo the parking lot
Outdoors · Chestertown
Chestertown, MD parks, trails & bike paths
Chestertown has 4 named parks and preserves on the map.
Conserved land, trails, parks and bike routes in Chestertown, measured from OpenStreetMap and USGS data.
At a glance
Chestertown outdoors
Conserved land
0.5%
10 of 1,889 acres
Trails
0.9 mi
0.3 mi per sq mi
Parks & preserves
4
2 conserved acres per 1,000 residents
Bike routes
2.1 mi
0.1 mi lanes · 2.0 mi off-road paths
Conserved land is a share of the whole town area. Bike lanes are often missing from the map in smaller towns, so that number is likely low.
Map
Conserved land, trails & bike routes
Tap a number or a place below to zoom in© OpenStreetMap contributors · USGS PAD-US
Places to walk
Parks & preserves with trails
Ranked by mapped trail miles. Directions go to the nearest marked trailhead or public parking.
2
Wilmer Park
Park
6 acres
Dog rules not recorded
DirectionsTo the parking lot
3
Village At Chestertown Park
Park
2 acres
Dog rules not recorded
DirectionsTo the parking lot
4
Fountain Park
Park
1 acres
Dog rules not recorded
DirectionsTo the parking lot
Things to do
Beaches, playgrounds, falls & more
Pick a kind of place for the list, directions, or pins on the map above.
Playgrounds in Chestertown
Water
Lakes & rivers
Tap a name for directions.
Who protects the land
10 conserved acres
Who manages it, from PAD-US. Approximate, because parcels can overlap.
Conserved doesn't always mean open to visitors. 5 acres are conservation easements, which are usually private land. Public access isn't recorded for 1 of 5 parcels. The places listed above are parks and preserves people visit.
Biking & sports
Bike routes, courts & fields
- Painted or protected bike lanes0.1 mi
- Off-road bike paths2.0 mi
- Shoulders & shared lanes0.0 mi
Courts & fields
- Tennis11
- Soccer3
- Baseball2
- Basketball1
Counts include school and college facilities, which aren't always open to the public.
Public lands
The biggest protected places in Chestertown
From USGS PAD-US: who manages each one and whether visitors are welcome.
Local Park 5 acConservation Easement 2 acUnknown Easement 2 acHistoric or Cultural Easement 1 ac
| Place | Managed by | Acres | Public access |
|---|---|---|---|
| Wilmer Park/lydia Hynson BoatLocal Park | Other or Unknown Local Government | 4 | Open |
| Fountain ParkLocal Park | Other or Unknown Local Government | 1 | Open |
History
Historic places to visit
Chestertown Historic DistrictDistrict
The Customs HouseBuilding
Truslow Boat HouseBuilding
Wide HallBuilding
Chestertown CemeteryCemetery
Trail talk
Conditions & tips from neighbors
No recent posts about Chestertown's trails yet. Muddy, icy, a bridge out, where to park: a quick post helps the next person.
Sources: trails, parks, preserves, courts and bike lanes © OpenStreetMap contributors (ODbL), map data as of 2026-09-28. Conserved land: USGS Gap Analysis Project, Protected Areas Database of the United States (PAD-US). Measured against the Census town boundary.
How we measure
"Trails" are OpenStreetMap paths, bridleways, public tracks and unpaved footways, plus footways inside a park or preserve or on a named trail route. Sidewalks are left out. Areas are counted on a 20-meter grid, so overlapping parcels count once. "Conserved" includes conservation easements, which protect land from development but are usually private property. Trailheads are the nearest marked trailhead, public parking lot or information board within about 150 meters of a preserve. Dog rules come from OpenStreetMap when someone has tagged them; otherwise we show what's typical for the land manager, or say the rules aren't recorded.