Hiking trails near Gloucester, Massachusetts

108 official trails lie within 25 miles of Gloucester — 297 miles in total, 96 rated easy and 4 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 373 ft; the median trail gains 63 ft.

Open the map on Gloucester

24 trails worth the drive

Trail	Miles	Climb	Difficulty	Drive from town
Ward Reservation	9.5	162 ft	Expert	49 min · 27 mi
Bay Circuit Trail	35.4	373 ft	Hard	43 min · 24 mi
Essex Railroad Rail Trail	18.6	194 ft	Hard	25 min · 17 mi
Border-To-Boston	25.2	162 ft	Moderate	52 min · 30 mi
Weir Hill	3.6	192 ft	Moderate	51 min · 30 mi
Rock Circuit Trail	3.7	144 ft	Moderate	47 min · 30 mi
Ravenswood Park	3.5	77 ft	Moderate	9 min · 4 mi
Castle Neck	5.8	70 ft	Moderate	27 min · 13 mi
Hog Island	3.5	171 ft	Moderate	16 min · 7 mi
Salem-Marblehead	4.5	74 ft	Easy	35 min · 20 mi
Bike-To-The-Sea	9.6	41 ft	Easy	38 min · 23 mi
Misery Islands	2.5	52 ft	Easy	19 min · 10 mi
4x4 trail	2.1	73 ft	Easy	11 min · 5 mi
Prospect Ledge Trail	1.6	164 ft	Easy	14 min · 8 mi
Bartholomew Hill Trail	1.8	119 ft	Easy	31 min · 16 mi
Bay Circut Trail	1.5	212 ft	Easy	49 min · 27 mi
Powow Riverwalk	3.6	64 ft	Easy	50 min · 29 mi
William Lloyd Garrison Trail	2.4	96 ft	Easy	46 min · 27 mi
Resdawg	1.7	98 ft	Easy	9 min · 4 mi
Indian Ridge Trail	1.4	51 ft	Easy	53 min · 31 mi
Yellow Diamond Trail	2.2	49 ft	Easy	40 min · 24 mi
Fernwood Lake Trail (Blue)	1.8	85 ft	Easy	9 min · 3 mi
Northern Strand Community Trail	3.7	34 ft	Easy	39 min · 23 mi
Cliffhanger	1.2	95 ft	Easy	13 min · 8 mi

Quick picks near Gloucester

Easy and short: Salem-Marblehead — 4.5 mi, rated easy, 13 mi from town
Biggest climb: Bay Circuit Trail — 373 ft over 35.4 mi, 18 mi from town
Longest: Bay Circuit Trail — 35.4 mi, 18 mi from town

What the trails reach

Summits: Ward Reservation to Holt Hill; Bay Circuit Trail to Holt Hill; Weir Hill to Weir Hill; Rock Circuit Trail to Black Rock

Lakes: Bay Circuit Trail to Berry Pond; Essex Railroad Rail Trail to Sutton Pond; Border-To-Boston to Parker River Reservoir; Weir Hill to Mill Pond Stevens Pond

Viewpoints: Rock Circuit Trail to Ziggy's Rock; Overlook Trail to Overlook

Beaches: Castle Neck to Crane Beach

Trail guides near Gloucester

Peabody Bikeway Part 1 — 3.4 mi, 36 ft climb · 17 mi away
Tri-Community Bikeway — 7.8 mi, 127 ft climb · 25 mi away
Mass Central/Wayside Rail Trail — 24.2 mi, 329 ft climb · 31 mi away
Skyline Trail — 4.4 mi, 415 ft climb · 32 mi away
Battle Road Trail (multi-purpose recreational path) — 5.1 mi, 90 ft climb · 35 mi away

Nearby towns: Amesbury (21 mi) · Boston (26 mi) · Lowell (32 mi) · Dover (40 mi)

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