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Running trails in Weymouth, MA
Weymouth has 11 trails in the directory — 4 paved and 2 on crushed gravel or dirt, 3 loops that return to the trailhead, 1 shaded, and 1 open 24 hours. 9 of them post opening hours, so you can check the gate before an early start. They're ranked here by rating weighted by review volume, across 1,243 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.
Webb Memorial State Park
4.7 ★★★★★ 641 reviews
Scenic peninsula park on Boston Harbor offering fishing, walking paths & city skyline views.
Great Esker Park
4.6 ★★★★★ 217 reviews
Glacial gravel ridge with canoe rentals, trails, playgrounds, sports fields & river views.
Bradford Hawes Park
4.4 ★★★★☆ 117 reviews
Public park with picnic areas, a playground, basketball and street hockey courts, and a baseball field.
Osprey Overlook Park
4.7 ★★★★★ 93 reviews
Dog-friendly park featuring paved paths, scenic views and trails.
King Oak Hill Park
4.7 ★★★★★ 90 reviews
Local park with a paved loop plus a grass field for picnics and kite flying.
House Rock Park
4.5 ★★★★★ 25 reviews
Union Point Wildlands Trust Trail
5 ★★★★★ 2 reviews
Fairing Way UNION POINT Nature Trail
5 ★★★★★ 1 reviews
No trails match those filters.
How to pick a trail in Weymouth
- Match the surface to your legs. Weymouth gives you a choice: 4 paved, 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 paved trails →
- Loop or out-and-back? 3 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.
- Check the hours before a 6am run. 1 trail in Weymouth is open 24 hours — the rest can sit inside a park that gates at dusk and doesn't unlock until well after sunrise. 9 of the 11 listings carry posted opening hours — worth a look before you set an alarm.
- Long run? Check water and restrooms first. 6 have trailhead parking, 2 have restrooms, and 2 have a water fountain in Weymouth. 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, 1 with mile markers, 4 that runners describe as quiet, 5 dog-friendly, and 3 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 Weymouth trails by type
Running trails near Weymouth
Worth the short drive — the closest towns with trails in the directory.