Looking for the best trails around Hebron?

Explore the best rated trails in Hebron, MD, whether you're looking for an easy walking trail or a bike trail like the Cross Island Trail and Marshyhope Hike and Bike Trail . With more than 32 trails covering 116 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

Junction & Breakwater Trail

Nice, but not completely paved as of Aug. 2025

August, 2025 by susancnett

The description of the trail says it is completely paved, but we started at the parking lot off of Wolfe Neck Road, and it is hard-pack, not paved. This was OK for us, but if we were on inline skates, we would not have been able to ride that section.

We rode northwest, towards Golden Eagle Blvd. After about a mile, it was paved. Traveling southeast, the surface was also hard-packed. We didn't go the whole way in that direction, so I don't know if it would have become paved at some point.
The trail is beautiful and well-marked. It was a Friday, midday, and the trail was busy. The road crossings were well-marked and had warning lights. The motorists were very respectful, waiting for trail users to cross.

I wish there were a few more signs with trail etiquette reminders. Twice, there were people stopped for a break and standing ON the trail, making passing them a challenge.

Kudos to Delaware for a great trail.

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.

Accordion

Kent Island South Trail

Kent Island South Trail

July, 2025 by carrollball99

I started riding this trail in 2018 and rode it 3-5 times a summer. It was a great trail that allowed you to get 12 miles in before riding the Cross Island Trail just 3 miles away. The tree roots have been bulging the asphalt for the past 7 years and now it is so bad I don't know if I will ride it again. For the first 1-2 miles from the start of either end the roots have the asphalt bulged up over two inches. Even riding with a suspension seat post the trail jars your spine unless you are standing on the foot pegs. Since the roots are so numerous this means you would be on the pegs 50 percent of the time. With the financial state that Maryland is in I doubt this trail will be repaired any time in the foreseeable future.

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.

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.

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.

Cross Island Trail

Cross Island extended

November, 2024 by smerchant1120

I frequently ride the Cross Island Trail. You can extend your ride starting at the Royal Farms. Continue on Sadler Rd when it ends make a left on Chester River Beach Rd then right on VFW Ave. At the Quality Inn make a left onto Winchester Creek Rd. Then right onto Hissey Rd and then left back onto Winchester Creek Road. Stop at Nesbit Rd. The roads are not busy and will add 4 more miles to your round trip.

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.

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