Looking for the best trails around Milford?

Explore the best rated trails in Milford, DE, whether you're looking for an easy walking trail or a bike trail like the Elephant Swamp Trail and Ben Cardin C&D Canal Recreational Trail . With more than 48 trails covering 152 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

Ben Cardin C&D Canal Recreational Trail

Ben Cardin C&D Canal Trail

April, 2024 by dillar

Great Trail with a seemless connection to Delaware’s Michael Castle Trail Paved the entire route, and “car width” wide. Parking at the Chesapeake City end is under the MD213 bridge. (The new paved lot mentioned in previous reviews is for the restaurant). Make sure it is not windy on your ride day. The canal is very wide and there is no windbreak, so a good tailwind turns into a terrible headwind on the way back. There are a couple switchbacks to get elevation gain but those are only for about 50’ of gain. Ice Cream shop right of the trail in St.GeorgesDE.opens the end of April.

Michael N. Castle C&D Canal Trail

Michael N. Castle C & D Canal Trail

November, 2023 by thejake91739

Q: If I bike ride the short 1.8 mile Ben Cardin trail in Maryland, should I bother continuing on to Delaware's Michael N. Castle trail?
A: Most definitely! Why stop after just two miles?

Q: Is it as flat and easy as the Ben Cardin trail?
A: It's mostly long, flat and occasionally curves as it parallels the not perfectly straight canal, but there are three places where the trail leaves the canal and climbs up the side of the hill. There it's curvier and takes you through woodlands and by a marina.

Q: Are the hills strenuous?
A: For regular, fit bikers and old guys like me with a Swytch pedal assist system, no. For others I would say yes.

Q: How strenuous?
A: One is steep enough to warrant two switchbacks. I also encountered a middle aged couple at the top of one of the hills resting, recovering, and acting like, What have we gotten ourselves into? I also observed another young, fit woman jogging who had to stop halfway up the hill, bend over, and put her hands on her knees.

Q:Is it picturesque?
A: Yes, lots of interesting photo ops of bridges, the canal, birds, woodlands, salt marshes, watercraft, charming homes, and historical sites.

Q: So if I start in Maryland and reach 5th Street in Delaware City, that's where I turn around?
A: Technically, that's the end of the Castle Trail, but why stop there? Cross the road and continue for another mile or so along quiet Canal Road and the Delaware City Marina to old, historic Delaware City, Battery Park, and Delaware Bay! You'll regret it if you don't!

Q: Are there any rest stops or restrooms?
A: There are restrooms at South Lums Trailhead on the trail and at Battery Park. There are also benches consistently along the canal about every 250 yards!

Q: Is it safe? What are the trail users like?
A: The friendliest and most polite you could ever hope for!

Q: As a former educator, what grade would you give this trail?
A: An A, but not an easy A. You'll have to work hard to complete those six inclines (assuming you're traveling the entire distance and doing a round trip).

Ben Cardin C&D Canal Recreational Trail

Ben Cardin C & D Canal recreation Trail

November, 2023 by thejake91739

Officially, this Maryland trail is only 1.8 miles, perfect for the fine folks of Chesapeake City or tourists to take a stroll out to the state line with Delaware and back. In fact, as I sat on the deck of the Ship Watch Inn across the canal from the path's trailhead the evening before I rode it, I saw so many people doing just that.

The 3.6 miles round trip is perfect for walkers since it is flat, quiet, and picturesque. When I started my bike ride the next morning at sunrise, all I encountered were runners and friendly dog walkers.

However, those of us on bikes aren't going to stop after two miles, so be sure to combine this with the Delaware portion of the canal trail for an additional twelve miles.

AND . . . don't stop after those twelve miles. Since you've already gone that far, continue across 5th Street in Delaware City into the park and then bear right toward Canal Street to travel another mile or so to historical Delaware City, Battery Park, and Delaware Bay! Total round trip of thirty miles.

WARNING: If you decide to continue on to Delaware City, there are three hills on Delaware's Ben Cardin Trail. Thank goodness for my Swytch pedal assist!

Accordion

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

Dennis Township Bike Path

24 miles from start to Cape May Point Lighthouse State Park

October, 2023 by tjfogelberg

I biked 2 miles South (Corson Tavern Road) from the Thousand Trails Lake and Shore campground (Oceanview) to the northern most trailhead and continued on to the Cape May Point Lighthouse State Park. What a great 24 mile ride! Very little interaction with cars. 100% paved (recent). This trail interacts with Middle Township and Cold Spring trail. Worth looking for...it was a bit tricky to find the trail heads. There was limited parking at a few of the trailheads. No restrooms on trail but I did see a few convenience stores along the way and also a city park (Railroad Avenue Park) closer to Cape May that had a bike station, drinking fountain and portable toilet.

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.

Dennis Township Bike Path

Nice narrow bike path

September, 2023 by joenad55

This was just completed in the last couple of years. A bit narrower than what I like to jog on, but this part goes all the way to the county line. The trees are set far back, which means this is in the sun most of the day. Would recommend going out early or late in the day. Have to cross a couple of roads with light traffic, and then Rt 83. Connects to the trail in Middle Township at the county line.

Smyrna-Clayton Bike Path

Community Connector

September, 2023 by jmcginnis12

Actually a small network of multi-use trails, the Smyrna-Clayton Bike Path gives residents of both of these communities a great alternative to walking or biking along busy local roads.
The trail is comprised of two main branches, starting from Duck Creek Parkway on either side of the High School and Middle School campus. The northwest branch separates the high school from adjacent mini-storage facilities and a residential subdivision, while the northeast division follows a powerline that runs along a branch of Duck Creek and connects to the west side of Smyrna via a footbridge. Both branches of the trail wrap around the campus and converge just south of a small cow pasture. The trail continues southeast of here, crossing the creek on a footbridge and ending at the intersection of Routes 6 and 300.
In addition to giving local residents a chance to enjoy nature, the trail gives students at the high and middle schools a safe means to walk to and from school . Unfortunately, I noticed some minor deterioration on the footbridge northwest of the Route 6 and 300 intersection. People who are sensitive to loud noises should also be aware that the local fire company's emergency alert siren is just north of the junction between the northwest and northeast branches of the trail.

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.

North Wildwood Seawall Trail

walking only

August, 2023 by 7d229h6b2k

Note that bikes, scooters and skates are not allowed on the Seawall. Walking trail only.

Cross Island Trail

Best easy ride

July, 2023 by kearns4fun

Loved this trail ride. Stayed cool on a hot day with all the canopy of greenery. Started in the nature park at west trail head and travelled east to Royal Farms. So many changes in scenery along the way. Well marked which is always a bonus. Would definitely recommend!!

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!

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