Looking for the best trails around Trappe?

Explore the best rated trails in Trappe, MD, whether you're looking for an easy walking trail or a bike trail like the Cross Island Trail and Strawberry Lake Way Bicycle Path . With more than 42 trails covering 183 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

BWI Trail

Long time user.

March, 2025 by eansel

Who ever scheduled work and approved the contactor to repair boardwalk bridge section along Telegraf Road should look for another job. New boards make it less safe than the old ones. A trip hazard and surface that may cause wheeled users to lose control. It is not improved but made less safe of a crossing for bikers, walkers, joggers, strollers, rollerbladers and skateboarders when they cross it. Almost like adding pot holes to asphalt. Just one persons comment.

BWI Trail

Great Ride with My Son – Smooth and Scenic BWI Trail (12.4 Miles)

March, 2025 by edris.shah

I biked the BWI Trail today with my son. We had a fantastic time. We covered 12.4 miles, and the trail was smooth, well-maintained, and easy to navigate. It loops around the airport, but you’d be surprised scenic it feels, with stretches of greenery, wooded areas, and even a few nice rest stops. Great for casual riders and pros alike. We’ll definitely be back for another ride.

Indian Head Rail Trail

Great Trail

March, 2025 by bf84rj842s

I’m a casual writer and I wrote the entire trail and one day.

Accordion

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.

BWI Trail

Didn't like it

March, 2025 by refresh7

I didn't really like this trail. You are traveling beside busy roads the majority of the time, breathing in car and jet fumes.

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.

South Shore Trail

not worth it

December, 2024 by mjmehalic

This “trail” is nothing more than a sidewalk behind a shopping center.

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.

Cross Island Trail

Walking out from the Kent Island Hyatt Hotel not very nice

October, 2024 by rebeccabeynon

We were on Kent Island for a wedding, and we took a stroll from the Hyatt Hotel in the direction away from the Bay Bridge. The trail runs alongside the busy road for a mile or so, then there’s a short stretch in a pleasant piney woods, and then back to the busy road. The trail is well maintained and the surface is good, and the part in the woods was pretty nice. But for most of our 3.5 mile walk (total, there and back) it was like walking beside a busy road. If I did this again, I’d try to access the trail at a place where you would have a nicer experience.

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.

Kent Island South Trail

Great Trail

July, 2024 by tpslucks

Liked the trail very much. However, I’ve seen other maps that show this trail actually begins on the north side of Rt-50 on the westbound side and connects to the trailhead. Is that portion part of this trail? It would make for a much longer route.

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