Hiking trails near Chestertown, Maryland

60 official trails lie within 25 miles of Chestertown — 147 miles in total, 58 rated easy and 1 hard or expert. Every distance and elevation figure below is computed from the agency centerline and a 10 m elevation model, not crowd-sourced.

The biggest climb nearby gains 437 ft; the median trail gains 37 ft.

Open the map on Chestertown

24 trails worth the drive

Trail	Miles	Climb	Difficulty	Drive from town
Mason Dixon Trail	36.2	437 ft	Hard	1 h 18 min · 50 mi
Broadneck Peninsula Trail	6.8	107 ft	Moderate	2 h 39 min · 111 mi
Stocksdale Trail	3.1	302 ft	Easy	1 h 55 min · 77 mi
Little Gunpowder Trail	3.0	140 ft	Easy	1 h 49 min · 72 mi
Lost Pond Trail	3.5	137 ft	Easy	1 h 55 min · 77 mi
White Banks Trail	1.9	229 ft	Easy	1 h 24 min · 50 mi
Beaver Marsh Loop	2.0	107 ft	Easy	1 h 24 min · 50 mi
West Side Trail	2.1	93 ft	Easy	1 h 43 min · 70 mi
Mauldin Mountain Loop	1.1	195 ft	Easy	1 h 22 min · 49 mi
Pond Loop	1.7	90 ft	Easy	1 h 21 min · 49 mi
Sandtown Trail	2.4	33 ft	Easy	50 min · 28 mi
Black Hill Red Trail	1.0	145 ft	Easy	1 h 13 min · 46 mi
Turkey Point Lighthouse Trail	1.3	93 ft	Easy	1 h 23 min · 51 mi
Jones Road Trail	1.4	49 ft	Easy	1 h 47 min · 74 mi
Watercress Farm Trail	1.8	66 ft	Easy	42 min · 25 mi
Winters Run Trail	1.2	123 ft	Easy	1 h 44 min · 70 mi
Mason-Dixon Trail	1.1	117 ft	Easy	1 h 25 min · 53 mi
Red Trail (Honeygo Run Regional Park)	1.1	84 ft	Easy	1 h 54 min · 79 mi
Little Florida Trail	1.4	49 ft	Easy	50 min · 28 mi
Wayne Gilchrest Trail	2.0	48 ft	Easy	3 min · 1 mi
Farm Road Trail	1.1	63 ft	Easy	1 h 22 min · 49 mi
Greenbrier Farm Trail	1.3	63 ft	Easy	42 min · 25 mi
Park Loop	3.5	30 ft	Easy	2 h 37 min · 109 mi
Whitetail Trail	1.2	34 ft	Easy	2 h 04 min · 82 mi

Quick picks near Chestertown

Easy and short: Stocksdale Trail — 3.1 mi, rated easy, 24 mi from town
Biggest climb: Mason Dixon Trail — 437 ft over 36.2 mi, 23 mi from town
Longest: Mason Dixon Trail — 36.2 mi, 23 mi from town

What the trails reach

Summits: Mason Dixon Trail to Bacon Hill; Mauldin Mountain Loop to Mauldin Mountain; Black Hill Red Trail to Black Hill

Lakes: Mason Dixon Trail to Plum Creek Pond; Broadneck Peninsula Trail to Hartings Ponds; West Side Trail to Atkisson Reservoir; Fitness Trail to Tuckahoe Lake

Viewpoints: Red Trail (Honeygo Run Regional Park) to Big Rocks; Park Loop to North Overlook

Mountain passes: Mason Dixon Trail to Susquehanna Point

Trail guides near Chestertown

Blue Trail (Loch Raven Reservoir Cooperative Wildlife Management Area) — 2.7 mi, 183 ft climb · 32 mi away
BCMSR Yellow Trail — 3.8 mi, 109 ft climb · 34 mi away
Rose Trail — 1.7 mi, 189 ft climb · 35 mi away
Ridge — 2.8 mi, 250 ft climb · 35 mi away
Torrey C Brown Rail Trail — 19.9 mi, 548 ft climb · 36 mi away
Grist Mill — 2.6 mi, 65 ft climb · 37 mi away
Loggers Trail — 2.1 mi, 233 ft climb · 38 mi away
Gray's Mill Trail — 3.3 mi, 238 ft climb · 38 mi away

Nearby towns: Aberdeen (21 mi) · Middletown (25 mi) · Annapolis (29 mi) · Baltimore (29 mi)

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