Fenwick Island, DE Walking Trails and Maps

196 Reviews

Looking for the best Walking trails around Fenwick Island?

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

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Activities
Length
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Type
27 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

Dennis Township Bike Path

2.4 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

North Wildwood Seawall Trail

0.8 mi
State: NJ
Concrete

Park Road Shared-Use Path

1.3 mi
State: DE
Asphalt

Prickly Pear Trail

3.5 mi
State: DE
Crushed Stone, Grass, Sand

Salt Marsh Spur

1.2 mi
State: DE
Sand

Seahorse Trail

1.3 mi
State: DE
Dirt

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
Accordion

Marshyhope Hike and Bike Trail

2.5 mi
State: MD
Asphalt, Gravel

Milton Rail-Trail

0.8 mi
State: DE
Asphalt

Seaside Nature Trail

0.7 mi
State: DE
Sand

Pinelands Nature Trail

1.5 mi
State: DE
Sand

American Holly Trail

0.7 mi
State: DE
Crushed Stone

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
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 that allows...
MD 4.9 mi Asphalt
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 at Raccoon...
DE 4.5 mi Boardwalk, Crushed Stone
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 park, but in...
DE 3.8 mi Asphalt, Concrete
The Cold Spring Bike Path runs along a segment of the former West Jersey & Seashore Railroad railbed. About the Route Starting at the southern endpoint of the Cold Spring Bike Path (sometimes...
NJ 2.7 mi Asphalt
The Dennis Township Bike Path can be found in Cape May County in South Jersey and is part of the Cape May County Trail Network. The trail begins on Woodbine Boulevard, behind the South Seaville Fire...
NJ 2.4 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
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 oceanside state...
DE 9.6 mi Asphalt
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 3.2 miles...
DE 3.2 mi Boardwalk, Crushed Stone
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 retreat,...
DE 8.3 mi Asphalt, Concrete
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 that once...
NJ 12.9 mi Asphalt
Along New Jersey's coast, a pathway atop a concrete sea wall provides a popular place for North Wildwood residents and visitors to enjoy ocean views. Beginning near 2nd Avenue and John F. Kennedy...
NJ 0.8 mi Concrete
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
The roughly 1-mile Salt Marsh Spur bisects the popular Walking Dunes Trail in Cape Henlopen State Park. The sand trail runs from the Biden Center, which offers meeting space and accommodations for...
DE 1.2 mi Sand
The Seahorse Trail runs primarily along the western edge of Holts Landing State Park. The trail provides access to the park’s campgrounds on its trek through dense forest. Connections to the...
DE 1.3 mi Dirt
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
Accordion
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
Redden State Forest, located just north of Georgetown in Sussex County, offers more than 44 miles of trails for hiking, mountain biking, birdwatching and hunting on several thousand acres. The most...
DE 4.6 mi Dirt
The Seaside Nature Trail in Cape Henlopen State Park takes visitors to the Seaside Nature Center around a nearly 1-mile rustic loop. A short stretch at the trail's northernmost point runs on a beach...
DE 0.7 mi Sand
The Pinelands Nature Trail, Delaware's first National Recreation Trail, is a 1.5-mile loop that follows a gentle grade through pine forest and cranberry bogs on a loose sand surface. Old artillery...
DE 1.5 mi Sand
Located in southern Delaware's Trap Pond State Park, the American Holly Trail provides a short and scenic alternative to some of the park's longer pathways. Trail users can start their journey from...
DE 0.7 mi Crushed Stone
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

Georgetown-Lewes Trail

J&B, Georgetown/Lewes and Cape Henlopen trails

July, 2025 by baarters

If you visit Lewes or Rehoboth Beach plan to take your bike and check out these trails. The J&B combined with Cape Henlopen SP is my favorite, be sure to ride it in both directions as well. This year I added the Georgetown section (it's a fair distance out and back from Lewes, ends up somewhere near Rt. 9 and Cool Spring Rd). The very straight, very flat paved Georgetown/Lewes Trail was busy close to Lewes on a warm Saturday in May, I expect summers are even more crowded. There are more road crossings than I like but cars were courteous. The J&B twists through both Lewes and Rehoboth with everything from paved residential areas to gravel paths through wooded and open field sections in between. The signage is adequate but it is easy to get misdirected in Rehoboth. If you make your way through Rehoboth on whatever route you choose, continue to the southern entrance of Cape Henlopen. You can't miss the Gordon Pond Trail which takes you through the park and back to Lewes. Cape Henlopen trails are well marked, there are multiple other trails within the park also. There are many places to stop and rest and bathrooms along all 3 sections.

Junction & Breakwater Trail

J&B, Cape Henlopen, and Georgetown/Lewes trails

July, 2025 by baarters

If you visit Lewes or Rehoboth Beach plan to take your bike and check out these trails. The J&B combined with Cape Henlopen SP is my favorite, be sure to ride it in both directions as well. This year I added the Georgetown section (it's a fair distance out and back from Lewes, ends up somewhere near Rt. 9 and Cool Spring Rd). The very straight, very flat paved Georgetown/Lewes Trail was busy close to Lewes on a warm Saturday in May, I expect summers are even more crowded. There are more road crossings than I like but cars were courteous. The J&B twists through both Lewes and Rehoboth with everything from paved residential areas to gravel paths through wooded and open field sections in between. The signage is adequate but it is easy to get misdirected in Rehoboth. If you make your way through Rehoboth on whatever route you choose, continue to the southern entrance of Cape Henlopen. You can't miss the Gordon Pond Trail which takes you through the park and back to Lewes. Cape Henlopen trails are well marked, there are multiple other trails within the park also. There are many places to stop and rest and bathrooms along all 3 sections.

Pinelands Nature Trail

very sandy

July, 2025 by hv8wkxq46x

I was looking for a trail run, and this was essentially like running on sand. Wasn’t a big fan. The other trails in the park are better.

Accordion

Middle Township Bike Path

Great Place to Train

July, 2025 by jstephens5

I connected this ride to the Cape May Loop and it was a fantastic way to get in some good miles in the morning hours. I rented a Trek Domane from the Surf & Buggy Center. The bike was great and they delivered it and picked it up. If you are looking to get some good training in during your stay this is the way to do it.

Junction & Breakwater Trail

Junction-Breakwater Trail

May, 2025 by cindy.mellott

We loved this trail. We went from Cape Henlopen to Rehoboth , then took this trail back to the campground. It was beautiful!!

413 Rail to Trail

Nice trail. Parking at either end of the trail. 1 port-a-potty at the trailheads. All asphalt & level just watch for upheavals in the trail in a couple of different places.

May, 2025 by debkalnins

Nice trail. Parking at either end of the trail. 1 port-a-potty at the trailheads. All asphalt & level just watch for upheavals in the trail in a couple of different places.

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!

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.

Dennis Township Bike Path

Seaville to Cape May

September, 2024 by cbrassington18

Parked at the Dennis Township Bike path train head. The parking area and trail were easy to find. However, there were only two marking spots in the small lot which could be an issue on busier weekends. Rode the trail to route 9 in Cape May before taking route 9 to the Lincoln Blvd beach entrance. The trail has quite a few road crossings on busy roads that will drop your average pace a fair bit. The trail is all paved and also includes mile markers at every .1 miles which is a very nice feature. Overall, a great trail to ride.

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!!

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