Looking for the best trails around Chincoteague?

Explore the best rated trails in Chincoteague, VA, whether you're looking for an easy walking trail or a bike trail like the American Holly Trail and Assawoman Canal Trail . With more than 8 trails covering 22 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.

Recent Trail Reviews

Bob Trail

Firm trail through the wood

October, 2023 by nphillips_tl

Firm fine gravel or dirt through the woods around the pond. A small section near the dam was paved. The south side is about 8 feet wide with gradual curves. The north side is about four feet wide and winds through the trees with a couple of sharp turns. We went counterclockwise out of the campground and found that to be downhill all the way around, or felt that way. Really no hills, just a slight up on the wider path for a short distance. We had two inch tires which were fine. One inch tires would probably be fine too. It was an enjoyable ride through the woods. Stop at the lovely church restored church

Assawoman Canal Trail

Greenway & Waterway

September, 2023 by jmcginnis12

Stretching a little over a mile along the west bank of the waterway for which it is named, the Assawoman Canal Trail offers a serene getaway for residents and visitors alike in the Bethany Beach area.
The trail is comprised of a crushed stone pathway suited to biking, walking, wheelchairs and pushing baby strollers that passes through environments that alternate between lush woodlands and grassy meadows. Some of the homes that the trail passes have beautifully landscaped yards (stay on the trail!) and small boats are a common site along the adjacent canal. Although the trail crosses Cedar Ave. at-grade (flashing signals alert motorists when trail users cross), it passes beneath Route 26 next to the canal, ending at Riga Drive.
In addition to providing an experience to enjoy nature and get in shape, the trail also makes it possible for residents of Ocean View and Cedar Neck to access businesses along Route 26 without walking along local roads. Plans eventually call for the trail to be extended further southeast, connecting to South Bethany.
The only things preventing me from giving the trail five stars are the high mosquito population in the warmer months of the year and lack of benches. The dead end at the northwest terminus of the trail also precludes access to Elliott Ave. and Back Bay Tours, limiting its potential to connect to communities there.

Fred Hudson Road Trail

Nice Trail Fred

June, 2023 by reesjb

Surprisingly pleasant trail - crushed stone/pine needle surface w/ plenty of shade. 1 mile out and back w/ ample parking at the trailhead. There are several other trails at the parking area as well. Flat and scenic stroll thru the pine woods and fresh pond waters. Most enjoyable!

Accordion

413 Rail to Trail

Great for biking

May, 2023 by sbabym

We did four miles yesterday and only saw four other bikers. Great flat path the shrubs and small trees along the path are beautiful but in some areas we had to go around because branches are growing over the path so if this isn’t maintained Mother Nature will take over and the path will be unusable and I would hate to see that happen! I don’t want to have to carry a machetes with me next time

Bob Trail

Nice Fall bike trail

October, 2022 by jamvjm

This was a nice ride to do in the fall. The route mostly went thru wooded areas. It was an easy mostly level ride over a gravel path that sometimes got narrow between the trees. It was 4.5 miles starting and ending at the nature center parking lot.

413 Rail to Trail

413 Rail Trail

July, 2022 by dakota26

My husband and I rode this trail and loved it. It's a flat and easy enjoyable ride. Very nice and clean parking areas at both ends. The trail did have some pine cones and branches that could be cleared. It may be in future plans as they expand; a port o potty would be useful. Overall kudos to those responsible for this trail.

Bob Trail

Nice Easy Ride

October, 2021 by beachbum25

Nice Ride through a State Park, I have been here on Many Weekday Afternoons after work & it has never been crowded. Main Trail Loops around Trap Pond & through the Campground, some Boardwalk, some Stone, Some narrower riding through the woods on Stone Dust. Plenty of other areas in the Park to ride as well. Easy to get 10 Miles in just cursing around the Park. Very Enjoyable

Assateague Island Bike Path

Great Ride

October, 2021 by beachbum25

I have ridden this Trail many times as I live on the Maryland Shore & Go to Assateague often, I never added it here as it isn't a True Rail Trail but noticed someone had so I'll put my $.02 in. Very Flat, only hill is the Bridge over the Bay. Can be quite windy so I usually Park at Visitor Center & Ride south first as this is generally into the wind, but be sure to check the Flag when you get there as it does sometimes turn abound. Horses may be seen anywhere on the Island....you will see plenty of Horse Droppings! There are 2 Bayside Access roads which are worth a visit, there is also a Bike Trail in the State Park Campground Area that is easy to get to. It ends at a gravel Parking lot near a Construction access gate Midway down Bayberry Drive, so you can get from one Trail to the other & add some variety to your ride. No Ocean Views from the Trail but there are plenty of spots where you can stop in The National Park Campground Loops & walk up over the Dunes. Trail Ends at OSV Zone, which requires a Permit. I often Bring My Jeep & make a Day of it here, but it gets VERY Crowded on Summer Weekends. You can always Bike in even when there are Massive Summer Backups on the Road. Easy to get 10 - 15 miles in here if you get Creative.

Prickly Pear Trail

Peaceful and pretty

August, 2021 by keylights

I’m staying in a beach house in a community across from the park entrance on the Coastal Highway. The written review is accurate. Nothing challenging, entirely flat. I’d say about 90% of the entire loop is in shade under the trees’ canopy. Walkers and bikers, but not crowded on a week-day mid-afternoon. Fun diversion from the beach. Four stars because it goes by fast on a bike passing mostly light forest, with one water view. Did two loops. Peaceful and pretty…

Prickly Pear Trail

Gem

August, 2021 by motbluehen

Tranquility at it’s finest! Love having this trail so close to home for the dogs too.

Assateague Island Bike Path

nice bike ride

July, 2021 by kitkat5578

Always a breeze, crossing the bridge is the best view of OC. Saw 4 wild ponies grazing, on my ride, right on the bike path… deer were all around as well. Wish it was longer ride and went by the beach !!!

413 Rail to Trail

413

July, 2021 by poconojack

We rode this 7/3/21 late morning and saw 5 other bikes and a few walking. Flat, straight, fun . Trail ends just before Crisfield and further down 413 there are bike lanes in town.

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