Running trails in Chesapeake, VA
Chesapeake has 13 trails in the directory — 1 paved and 2 on crushed gravel or dirt, 2 loops that return to the trailhead, 2 with a stated distance, 4 shaded, and 1 open 24 hours. 8 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 9,691 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.
Chesapeake City Park
4.7 ★★★★★ 3,376 reviews
Pine forest featuring open space for dog & skate parks plus an expansive playground & horseshoes.
Oak Grove Park
4.7 ★★★★★ 2,851 reviews
This 65-acre outdoor activity place has a 1.5-mi. path around a lake, plus benches & a playground.
Deep Creek Park
4.6 ★★★★★ 881 reviews
City park with several ball fields, a dog run, playground, walking trail & picnic/grilling areas.
Great Bridge Lock Park
4.5 ★★★★★ 852 reviews
Island park featuring a playground, fishing area, boat ramp, observation beam & picnic shelters.
Indian River Park South Side
4.4 ★★★★☆ 829 reviews
91-acre forested park providing a playground, sports field & miles of mountain biking/hiking trails.
Deep Creek Lock Park
4.5 ★★★★★ 427 reviews
25 acres of waterfront woods with a canoe launch, volleyball courts, picnic shelters & a play area.
Bells Mill Park
4.3 ★★★★☆ 302 reviews
A former landfill, this park now offers wetlands & meadows with a 2.5-mile trail & picnic areas.
Northwest River Natural Area Preserve
4.8 ★★★★★ 83 reviews
This 2,774-acre nature preserve features forests & swamps, plus rare plants & animals.
Black Bear Trail Bridge 2
4.1 ★★★★☆ 9 reviews
Marsh & marsh overlook Trailhead
5 ★★★★★ 2 reviews
No trails match those filters.
How to pick a trail in Chesapeake
- Match the surface to your legs. Chesapeake gives you a choice: 2 natural surface, 1 paved, 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 Chesapeake is Bells Mill Park at 2.5 mi.
- Check the hours before a 6am run. 1 trail in Chesapeake is open 24 hours — the rest can sit inside a park that gates at dusk and doesn't unlock until well after sunrise. 8 of the 13 listings carry posted opening hours — worth a look before you set an alarm. 1 is lit, which is what you want for winter evenings.
- Long run? Check water and restrooms first. 7 have trailhead parking, 7 have restrooms, and 1 has a water fountain in Chesapeake. Anything over an hour and those stop being nice-to-haves — and in summer, shade counts double.
- The small things that decide it. 4 shaded, 1 with mile markers, 5 that runners describe as quiet, 6 dog-friendly, and 5 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 Chesapeake trails by type
- Natural surface trails
- Paved trails
- Mixed trails
- Loop trails
- Shaded trails
- Lit for early & night runs
- Flat & fast
- Hilly trails
- Scenic trails
- Trails with restrooms
- Trails with water fountains
- Trailhead parking
- Trails with mile markers
- Quiet, uncrowded trails
- Dog-friendly
- Stroller & wheelchair-accessible
Running trails near Chesapeake
Worth the short drive — the closest towns with trails in the directory.