Looking for the best trails around Deal Island?

Explore the best rated trails in Deal Island, MD, whether you're looking for an easy walking trail or a bike trail like the Three Notch Trail and Chesapeake Beach Railway Trail . With more than 13 trails covering 60 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

Parking

October, 2025 by jayneweinhold

Nice ride up to Lewis mid October. There is a new, large paved parking lot on Cool Spring Rd, just past the intersection at Rt 9. Need to cross Rt 9 to get to the trail, so caution is needed. Pretty ride through the tree shaded area, less so the closer you get to Lewis where it’s a lot busier.

Georgetown-Lewes Trail

UPDATE YO MY POST

September, 2025 by emfref_tl

Not 5 star from Lewes (Route 1) to Georgetown..

Georgetown-Lewes Trail

A Bit Disappointed

September, 2025 by emfref_tl

I thought the trail to Georgetown was fully completed… if it is… it’s NOT clearly marked. From Lewes the signs stop at some point and one is left to ride on Route 9 with major traffic (wide shoulder - but noisy)! Then Georgetown has NO signs letting you know where the trail is… eventually found Ingramtown Road to Airport Road. But when you get to Airport Road… there is no information where to go… so I headed to Route 9 and road the busy road back to Lewes. sign telling you to go right or left… uh

Accordion

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.

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.

Three Notch Trail

Three years later

September, 2024 by c8

BARN CATS STILL THERE! I couldn't believe it. Again, one was laying on the trail, just as chill as could be. An hour later, it was still there! Must have become jaded with all the attention it must get, b/c it didn't care about my presence, or the little pat I gave it, lol.
Trail is still a pleasant getaway in the country. Very little traffic on the trail on an early Saturday evening. Still in good shape. Some bumps in it now, from tree roots, but they are few and far between. Wish I could live along this trail.

Easton Rails-to-Trails

Very lovely in-town trail!

July, 2024 by tpslucks

While the trail in town is very lovely, relatively short, it’s very clean and enough meandering through green space, I really enjoy the less known western spur more. That trail spur on the opposite side of Easton Parkway is really awesome. I love riding through the well laid curves and tree canopies. Enough trail benches and smooth pavement. Love it!

Three Notch Trail

Beautiful Country Views…

June, 2024 by allen.tinasia

I haven’t seen any recent reviews regarding this location so I wanted to write an update. I am an inline skater & enjoy new trails to try. It’s a beautiful location for the most part. Very quiet & a nice long trail with minimum elevation. It is surrounded by an Omish community, & farmlands throughout the entire route. Although it was beautiful views of the land & farms, it also had downsides. The roads were not very smooth, but still nice enough to skate on. There was animal poop all on the trail you have to avoid if you care about your wheels. It also smells like farmland. Do with that as you wish. Happy Riding!

Easton Rails-to-Trails

love the trail!

June, 2024 by tpslucks

Very nice trail. I just discovered the western spur the other day and it’s very nice. Was curious that it’s not on the trail map though.

Chesapeake Beach Railway Trail

nice easy walk with good views.

January, 2024 by 737doc

Trail requires a short walk through a parking lot to reach the boardwalk trail head. TrailLink said parking was available in the neighboring neighborhoods of richfield station and bayview hills, this is incorrect. We couldn't find any parking in richfield station and bayview hills was marked with multiple private property no trespassing signs as well as painted reserved spots for residents, and is clearly a private community not set up for trail parking. We went on the towns website and found parking as described behind kellams field adjacent to the water park. The trail is well maintained and easy to walk as there is very little elevation change. It is a nice amenity but isn't a day hike or time consuming activity, nice for a quick easy walk with some nice views. There was one loose dog someone felt they didn't need to have leashed, and some fast moving bicycle traffic that was quite close on the boardwalk section. The bicycles may or may not warn you of their impending passing so be aware.. The water views are nice and offer some good photo ops for birds.

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

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