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Running trails in Pittsfield, MA
Pittsfield has 11 trails in the directory — 2 on crushed gravel or dirt, 2 loops that return to the trailhead, 2 with a stated distance, 1 shaded, and 5 open 24 hours. Every one post opening hours, so you can check the gate before an early start. They're ranked here by rating weighted by review volume, across 1,031 Google reviews. Filter by surface, loop, distance, shade or lighting to get to the run you're actually planning — no made-up difficulty score, just the facts you'd check before driving out.
Springside Park
4.1 ★★★★☆ 278 reviews
Familiar hangout featuring tranquil gardens, a pond & an arboretum, plus ball fields & picnic spots.
Pittsfield State Forest
4.5 ★★★★★ 231 reviews
Large, wooded state park with hiking trails, campsites & a pond for boating, swimming & fishing.
Mass Audubon Canoe Meadows Wildlife Sanctuary
4.6 ★★★★★ 217 reviews
Nature preserve with trails for hiking, cross-country skiing and wildlife-watching.
Kirvin Park
4.3 ★★★★☆ 153 reviews
Local park featuring picnic tables and a playground, as well as wooded areas with trails and a waterfall.
Barkerville Conservation Area
4 ★★★★☆ 16 reviews
Start Taconic Crest Trail - Southern Terminus
4.6 ★★★★★ 5 reviews
No trails match those filters.
How to pick a trail in Pittsfield
- Match the surface to your legs. Pittsfield gives you a choice: 2 natural surface and 1 mixed. Asphalt and concrete are fast, predictable and runnable year-round but the least forgiving; crushed limestone and dirt take the sting out of high mileage; boardwalk is flat and scenic but slick in the wet. If your shins or knees are complaining, the fix that actually works is varying the surface you run on rather than chasing one "best" one. More natural surface trails →
- Loop or out-and-back? 2 trails here are loops, so you finish back at the car with no backtracking — the easiest way to run a set distance without thinking about it. On an out-and-back you turn round at half your target distance, which makes any trail fit any run. The longest stated distance in Pittsfield is The Boulders Reserve - Dalton Ave Trailhead at 7 mi. 1 trail is long enough for a 5-mile-plus run without repeating yourself.
- Check the hours before a 6am run. 5 trails in Pittsfield are open 24 hours — the rest can sit inside a park that gates at dusk and doesn't unlock until well after sunrise. 11 of the 11 listings carry posted opening hours — worth a look before you set an alarm.
- Long run? Check water and restrooms first. 3 have trailhead parking and 2 have restrooms in Pittsfield. Anything over an hour and those stop being nice-to-haves — and in summer, shade counts double.
- The small things that decide it. 1 shaded, 5 with mile markers, 2 that runners describe as quiet, 3 dog-friendly, and 4 smooth and wide enough for a stroller or a wheelchair. Busy or quiet isn't a good-or-bad thing here: a busy path is the safer choice for a solo run at dawn, a quiet one is better for intervals.
More on all of this in the trail-running guides.
Browse Pittsfield trails by type
Running trails near Pittsfield
Worth the short drive — the closest towns with trails in the directory.