Looking for the best trails around Pittsville?

Explore the best rated trails in Pittsville, MD, whether you're looking for an easy walking trail or a bike trail like the Cold Spring Bike Path and Marshyhope Hike and Bike Trail . With more than 24 trails covering 73 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

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.

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.

Accordion

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!!

Milton Rail-Trail

lovely semi-forested, pathed walk

July, 2024 by christine.m.layton

This trail goes through forest, field, and some pretty neighborhoods. Excellent for Pokemon players, dog walkers, and meanderers.

Seaside Nature Trail

Sandy Path Through The Coastal Forest

July, 2024 by jmcginnis12@gmail.com

Part of the Cape Henlopen State Park trail network, the Seaside Nature Trail branches off the Cape Henlopen State Park Bike Loop at the nature center and gives visitors the opportunity to explore the pine barrens, scrublands and a portion of beach on the Delaware Bay on the park's north side. Although the sandy surface of the trail is loose in some sections and poorly suited to cycling, it offers a peaceful and picturesque hiking experience. Highlights include the entrance to a World War II-era bunker, whose overgrown and decaying gate resembles a scene from a post-apocalyptic movie, the panoramic views along the Delaware Bay and the crab statues in front of the nature center. Trail users should also check out the nature center itself to learn more about the wildlife they may encounter and the state park's fishing pier and bait & tackle shop are just a short walk down the beach at Delaware Bay.

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!

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.

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

Assawoman Canal Trail

Greenway & Waterway

September, 2023 by jmcginnis12

Stretching a little over a mile along the west bank of the waterway for which it is named, the Assawoman Canal Trail offers a serene getaway for residents and visitors alike in the Bethany Beach area.
The trail is comprised of a crushed stone pathway suited to biking, walking, wheelchairs and pushing baby strollers that passes through environments that alternate between lush woodlands and grassy meadows. Some of the homes that the trail passes have beautifully landscaped yards (stay on the trail!) and small boats are a common site along the adjacent canal. Although the trail crosses Cedar Ave. at-grade (flashing signals alert motorists when trail users cross), it passes beneath Route 26 next to the canal, ending at Riga Drive.
In addition to providing an experience to enjoy nature and get in shape, the trail also makes it possible for residents of Ocean View and Cedar Neck to access businesses along Route 26 without walking along local roads. Plans eventually call for the trail to be extended further southeast, connecting to South Bethany.
The only things preventing me from giving the trail five stars are the high mosquito population in the warmer months of the year and lack of benches. The dead end at the northwest terminus of the trail also precludes access to Elliott Ave. and Back Bay Tours, limiting its potential to connect to communities there.

Easton Rails-to-Trails

Pleasant ride on a hot afternoon

August, 2023 by fisher1_tl

We just got back from a ride. Parked at the north end of the trail, and rode to the southern end and back. Took a detour through the new John F. Ford park, which was a nice surprise. Except for a few tree root speed bumps and some hickory nuts, the paved trail was in very good condition. More than half is shaded in the afternoon. Passed a few pedestrians, but had the trail mostly to ourselves. Not a trail to go speed riding, as there are frequent gates at road crossings.

Fred Hudson Road Trail

Nice Trail Fred

June, 2023 by reesjb

Surprisingly pleasant trail - crushed stone/pine needle surface w/ plenty of shade. 1 mile out and back w/ ample parking at the trailhead. There are several other trails at the parking area as well. Flat and scenic stroll thru the pine woods and fresh pond waters. Most enjoyable!

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.