Looking for the best trails around Dewey Beach?

Explore the best rated trails in Dewey Beach, DE, whether you're looking for an easy walking trail or a bike trail like the Pleasantville to Somers Point Bike Path and Maurice River Bikeway Trail . With more than 39 trails covering 110 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

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!!

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.

Isaac Branch Greenway Trail

This is a really nice trail for a quick ride on any kind of bike. Really enjoyed it today wish it was longer.

February, 2025 by reram2224

This is a really nice trail for a quick ride on any kind of bike. Really enjoyed it today wish it was longer.

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.

Maurice River Bikeway Trail

This is a good place to hike all the trails for a couple hours! Great views!

January, 2025 by tcdowns72

This is a good place to hike all the trails for a couple hours! Great views!

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.

Find Nearby City trails

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 40,000 miles of trail maps
  • Share your trail photos
  • Save your own favorite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Get the Free TrailLink App

The trail is always better with TrailLink

Scan the QR code to get TrailLink on your phone

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

Log in with Apple

OR

Register for free!

Join TrailLink (a non-profit) to view more than 40,000 miles of trail maps and more!

Register with Google

Register with Apple

OR

Your account has been deleted.