Ocean Pines, MD Bike Trails and Maps

179 Reviews

Looking for the best Bike trails around Ocean Pines?

Find the top rated bike trails in Ocean Pines, whether you're looking for an easy short bike trail or a long bike trail, you'll find what you're looking for. Click on a bike trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
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Type
19 Results
Activities
Length
Surfaces
Type

413 Rail to Trail

4.5 mi
State: MD
Asphalt, Crushed Stone

Assateague Island Bike Path

4.9 mi
State: MD
Asphalt

Bob Trail

4.5 mi
State: DE
Boardwalk, Crushed Stone

Cape Henlopen State Park Bike Loop

3.8 mi
State: DE
Asphalt, Concrete

Cold Spring Bike Path

2.7 mi
State: NJ
Asphalt

Fred Hudson Road Trail

1.6 mi
State: DE
Asphalt, Crushed Stone

Georgetown-Lewes Trail

9.6 mi
State: DE
Asphalt

Gordons Pond Trail

3.2 mi
State: DE
Boardwalk, Crushed Stone

Junction & Breakwater Trail

8.3 mi
State: DE
Asphalt, Concrete

Middle Township Bike Path

12.9 mi
State: NJ
Asphalt

Park Road Shared-Use Path

1.3 mi
State: DE
Asphalt

Prickly Pear Trail

3.5 mi
State: DE
Crushed Stone, Grass, Sand

Walking Dunes Trail

2.6 mi
State: DE
Crushed Stone

Wildwood Crest Bike Path

1 mi
State: NJ
Asphalt, Concrete

Assawoman Canal Trail

1.2 mi
State: DE
Crushed Stone

Killens Pond Bike Trail

2 mi
State: DE
Asphalt, Concrete, Crushed Stone

Marshyhope Hike and Bike Trail

2.5 mi
State: MD
Asphalt, Gravel

Milton Rail-Trail

0.8 mi
State: DE
Asphalt

Mispillion River Greenway

1.8 mi
State: DE
Boardwalk, Concrete
Trail Image Trail Name States Length Surface Rating
The 413 Rail to Trail is located in Somerset County, Maryland. The trail will be 12 miles point-to-point when complete. The trail parallels State Route 413, which lends it its name, and is built in...
MD 4.5 mi Asphalt, Crushed Stone
Overview Long known for its sandy beaches and wild pony herds, beautiful and remote Assateague Island has become more bike-friendly thanks to the construction of a 4.9-mile paved, multi-use trail...
MD 4.9 mi Asphalt
Overview The Bob Trail (or simply, The Bob) in Trap Pond State Park loops around the perimeter of the 90-acre Trap Pond for 4.5 miles. The trail winds through hardwood forests, crosses a scenic dam...
DE 4.5 mi Boardwalk, Crushed Stone
Overview Cape Henlopen State Park, on Delaware’s Atlantic coastline, is one of the state’s must-see destinations. William Penn (founder of Pennsylvania) once owned much of the land that’s now the...
DE 3.8 mi Asphalt, Concrete
The Jersey shore was a major vacation destination for residents of the Delaware Valley region throughout the early 20th century. From the 1890s to 1930s, two parallel railroad lines—the Atlantic City...
NJ 2.7 mi Asphalt
The Fred Hudson Road Trail is a mixture of asphalt sidepath and wooded crushed stone trail, running from the outskirts of the quiet town of Ocean View to the even quieter scenic remove of the Delaware...
DE 1.6 mi Asphalt, Crushed Stone
Overview    Currently open in segments, the Georgetown-Lewes Trail takes a its relatively flat route that runs through tree-lined countryside into the coastal town of Lewes before ending in an...
DE 9.6 mi Asphalt
Overview The Gordons Pond Trail is located in Cape Henlopen State Park, where it skirts the western side of Gordons Pond, a 900-acre salt water lagoon. The finely crushed gravel pathway winds for...
DE 3.2 mi Boardwalk, Crushed Stone
Overview The Junction & Breakwater Trail follows a section of the former Penn Central railroad, connecting the Delaware beach towns of Rehoboth Beach and Lewes. The 8.3-mile trail acts as a nature...
DE 8.3 mi Asphalt, Concrete
Overview The Jersey Shore was a major vacation destination for residents of the Delaware Valley region throughout the early 20th century; the Middle Township Bike Path follows a former rail line...
NJ 12.9 mi Asphalt
Located on the marshy northern outskirts of the coastal community of Lewes, the Park Road Shared-Use Path provides a nice stretch of paved trail for cyclists and pedestrians to aid in navigating the...
DE 1.3 mi Asphalt
The Prickly Pear Trail is a 3.5-mile loop in Delaware Seashore State Park’s Fresh Pond area. The trail runs through young forest and open meadows, with the eastern stretch featuring a crushed stone...
DE 3.5 mi Crushed Stone, Grass, Sand
True to its name, the Walking Dunes Trail offers a pleasant hike through the dunes of Cape Henlopen State Park—specifically the “walking dunes,” which slowly move across the park. Unlike some of the...
DE 2.6 mi Crushed Stone
The Wildwood Crest Bike Path is a one-mile bike path that runs along the beach from East Cresse Avenue to East Rambler Road.
NJ 1 mi Asphalt, Concrete
The Assawoman Canal Trail is a crushed stone pathway for cyclists and pedestrians that runs along the west side of its namesake waterway through Ocean View, Delaware. The canal was hand-dug in 1891...
DE 1.2 mi Crushed Stone
The Killens Pond Bike Trail provides non-motorized access from US 13 to Killens Pond State Park. The short trail parallels Killens Pond Road before turning south into the park along its main access...
DE 2 mi Asphalt, Concrete, Crushed Stone
The Marshyhope Creek is a 37-mile tributary of the Nanticoke River running from Delaware to Maryland. One of the towns it passes through is Federalsburg, Maryland, where a 2.5-mile multiuse greenway...
MD 2.5 mi Asphalt, Gravel
The Milton Rail-Trail is a short, paved pathway in the small town of Milton, allowing local residents to get out and take a quick ride or walk along a flat, off-road corridor. The newest section of...
DE 0.8 mi Asphalt
The Mispillion River Greenway runs through historic downtown Milford on both sides of the Mispillion River. The greenway, which is surfaced primarily with brick and concrete, provides scenic views of...
DE 1.8 mi Boardwalk, Concrete

Recent Trail Reviews

Redden State Forest Headquarters Loop Trail

Free and accessible.

March, 2025 by mih28271

An amazing free resource for the lower eastern shore. Flat sand trail mostly covered with pine needles. I would not recommend this trail if your tires are less than 50mm (2 inch) wide. Minimal but effective main trail markings. Multiple unmarked side trails. Adequate parking. Pack a lunch and make a day of it. This is a state forest not a park, there are port-a-john's near the parking area.

Milton Rail-Trail

Beautiful but leaves you wanting more

January, 2025 by tymetravler

We live in Milton and have visited the trail several times. Each time I think how awesome it would be if it connected to the larger trail system leading into Lewes, Cape Henlopen State Park, and Rehoboth. On occasion, we will get into the car and drive to one of those trailheads. The Milton rail trail is beautiful, but maybe be a little shortsighted for those wanting more of a workout/challenge/enjoyment.

Middle Township Bike Path

Not much to see but the Zoo was a bonus

October, 2024 by adab

This trail is well maintained & marked but there isn’t much to see as it follows the power lines through no man’s land. However!, the Cape May Zoo was really nice & free!

Accordion

Gordons Pond Trail

Beautiful & just enough

October, 2024 by adab

This is a well maintained trail, flat, varied scenery with a great long boardwalk/ bridge. Nice stops in a few sites with some history. Beach view / marsh / birds. Well traveled with bikers & walkers on a Sunday fall afternoon. 6.4 miles round trip with a strong wind on the way back had me sweating.

Cold Spring Bike Path

Straight paved trail. Connects to two other trails.

September, 2024 by nnesky

We bicycled the Cold Spring Bike Path, the Middle Township Bike Path and the Dennis Township Bike Path. They are fully connected, paved and straight. It's like a highway from north to south. It follows the power lines and is mostly sunny. There's very little to see along the way. It's great for exercise - bicycling, jogging, inline skating, pushing a stroller. The best part - no cars!!

Middle Township Bike Path

nice surprise.

August, 2024 by fc9vjs5dw4

I was happy to ride this path because it was asphalt. Just wow! The path is so well maintained. The brush is kept trimmed and about 3 ft back from the wide paved path. The mile markers are painted every 10th on the ground. This was such a pleasant ride!!!!

Milton Rail-Trail

lovely semi-forested, pathed walk

July, 2024 by christine.m.layton

This trail goes through forest, field, and some pretty neighborhoods. Excellent for Pokemon players, dog walkers, and meanderers.

Seaside Nature Trail

Sandy Path Through The Coastal Forest

July, 2024 by jmcginnis12@gmail.com

Part of the Cape Henlopen State Park trail network, the Seaside Nature Trail branches off the Cape Henlopen State Park Bike Loop at the nature center and gives visitors the opportunity to explore the pine barrens, scrublands and a portion of beach on the Delaware Bay on the park's north side. Although the sandy surface of the trail is loose in some sections and poorly suited to cycling, it offers a peaceful and picturesque hiking experience. Highlights include the entrance to a World War II-era bunker, whose overgrown and decaying gate resembles a scene from a post-apocalyptic movie, the panoramic views along the Delaware Bay and the crab statues in front of the nature center. Trail users should also check out the nature center itself to learn more about the wildlife they may encounter and the state park's fishing pier and bait & tackle shop are just a short walk down the beach at Delaware Bay.

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.

North Wildwood Seawall Trail

walking only

August, 2023 by 7d229h6b2k

Note that bikes, scooters and skates are not allowed on the Seawall. Walking trail only.

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!

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