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 35 trails covering 117 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.
The Wayne Gilchrest Trail, which opened on Earth Day in 2012, runs along the southern edge of the historic Maryland Eastern Shore community of Chestertown. The trail connects Washington College to the...
The Mispillion River Greenway runs through historic downtown Milford on both sides of the Mispillion River. The greenway, which is surfaced primarily with brick and concrete, provides scenic views of...
The Jersey shore was a major vacation destination for residents of the Delaware Valley region throughout the early 20th century. From the 1890s to 1930s, two parallel railroad lines—the Atlantic City...
The Seahorse Trail runs primarily along the western edge of Holts Landing State Park. The trail provides access to the park’s campgrounds on its trek through dense forest. Connections to the...
Maryland's Ben Cardin C&D Canal Recreational Trail links to Delaware's Michael Castle Trail; both run along the north bank of the Chesapeake and Delaware (C&D) Canal and meet at the state line. The...
The Gordons Pond Trail is located in Cape Henlopen State Park, where it skirts the western side of Gordons Pond, a 900-acre salt water lagoon. The finely crushed gravel pathway winds through coastal...
The Michael Castle Trail offers a scenic 12-mile route along the north shore of the Chesapeake and Delaware Canal in northern Delaware. The trail is named after the former governor and US...
The Loblolly Trail in Trap Pond State Park loops around the perimeter of the 90-acre Trap Pond. The trail winds through hardwood forests, crosses a scenic dam at Raccoon Pond and travels over...
Maryland's Cross Island Trail spans Kent Island, east to west, in Queen Anne's County, providing multiple points of access to everything from libraries and schools to ball fields and the waterfront....
True to its name, the Walking Dunes Trail offers a pleasant hike through the dunes of Cape Henlopen State Park—specifically the “walking dunes,” which slowly move across the park. Unlike some of the...
Ocean City Bike Path offers a short, paved route through the center of Ocean City and allows visitors a glimpse into the history of this interesting seaside town. The trail parallels Haven Avenue...
The St. Michaels Nature Trail skirts the western edge of the scenic town of St. Michaels, Maryland, which was built on the site of a 17th century Anglican church that eventually lent the settlement...
This beautiful, pine-studded rail-trail winds through Cape Henlopen State Park next to wetlands and farmland, offering a break from the nearby beaches and eclectic shopping areas. The trail runs from...
The Easton Rails to Trails runs from Dutchmans Lane in southern Easton, Maryland, to North Easton Parka large sports complexover 2.5 miles away. The trail opened in 1998 and has been a popular local...
The Marshyhope Creek is a 37-mile tributary of the Nanticoke River running from Delaware to Maryland. One of the towns it passes through is Federalsburg, Maryland, where a 2.5-mile multiuse greenway...
This community trail begins at the intersection of Main and Pearl streets in the town of Port Norris, near the mouth of the Maurice River. It connects Port Norris with Bivalve. At one time the area...
Along New Jersey's coast, a pathway atop a concrete sea wall provides a popular place for North Wildwood residents and visitors to enjoy ocean views. Beginning near 2nd Avenue and John F. Kennedy...
The Kent Island South Trail is one of two popular recreational trails (along with the Cross Island Trail) on Maryland's Kent Island, the largest island in the Chesapeake Bay. The trail runs parallel...
The Woodbine Railroad Trail occupies the right-of-way of a former Pennsylvania and Reading Railroad line. The paved pathway traverses Woodbine as it parallels Dehirsch Avenue; a wide grassy median...
The Prickly Pear Trail is a 3.5-mile loop in Delaware Seashore State Park’s Fresh Pond area. The trail runs through young forest and open meadows, with the eastern stretch featuring a crushed stone...
The Mispillion River Greenway runs through historic downtown Milford on both sides of the Mispillion River. The greenway, which is surfaced primarily with brick and concrete, provides scenic views of...
Cape May’s 8.9-mile Middle Township Bike Path and 2.7-mile Cold Spring Bike Path were fully connected in summer 2017. Riders can begin their journey at US 9/Sandman Boulevard in Lower Township across...
This community trail begins at the intersection of Main and Pearl streets in the town of Port Norris, near the mouth of the Maurice River. It connects Port Norris with Bivalve. At one time the area...
The Kent Island South Trail is one of two popular recreational trails (along with the Cross Island Trail) on Maryland's Kent Island, the largest island in the Chesapeake Bay. The trail runs parallel...
The Bike Loop in Cape Henlopen State Park is a nearly 3.5-mile paved trail through the scenic park. The loop offers various branches that lead off into the marshes with wide vistas of the Atlantic...
The Loblolly Trail in Trap Pond State Park loops around the perimeter of the 90-acre Trap Pond. The trail winds through hardwood forests, crosses a scenic dam at Raccoon Pond and travels over...
The Wayne Gilchrest Trail, which opened on Earth Day in 2012, runs along the southern edge of the historic Maryland Eastern Shore community of Chestertown. The trail connects Washington College to the...
The Easton Rails to Trails runs from Dutchmans Lane in southern Easton, Maryland, to North Easton Parka large sports complexover 2.5 miles away. The trail opened in 1998 and has been a popular local...
As you walk along the Elephant Swamp Trail, it’s easy to see where it picked up the swamp part of its name. As for the rest, legend has it that in the late 1800s, an elephant got loose in the swamp...
The roughly 1-mile Salt Marsh Spur bisects the popular Walking Dunes Trail in Cape Henlopen State Park. The sand trail runs from the Biden Center, which offers meeting space and accommodations for...
Ocean City Bike Path offers a short, paved route through the center of Ocean City and allows visitors a glimpse into the history of this interesting seaside town. The trail parallels Haven Avenue...
Maryland's Ben Cardin C&D Canal Recreational Trail links to Delaware's Michael Castle Trail; both run along the north bank of the Chesapeake and Delaware (C&D) Canal and meet at the state line. The...
The Michael Castle Trail offers a scenic 12-mile route along the north shore of the Chesapeake and Delaware Canal in northern Delaware. The trail is named after the former governor and US...
Maryland's Cross Island Trail spans Kent Island, east to west, in Queen Anne's County, providing multiple points of access to everything from libraries and schools to ball fields and the waterfront....
The Seahorse Trail runs primarily along the western edge of Holts Landing State Park. The trail provides access to the park’s campgrounds on its trek through dense forest. Connections to the...
Along New Jersey's coast, a pathway atop a concrete sea wall provides a popular place for North Wildwood residents and visitors to enjoy ocean views. Beginning near 2nd Avenue and John F. Kennedy...
This beautiful, pine-studded rail-trail winds through Cape Henlopen State Park next to wetlands and farmland, offering a break from the nearby beaches and eclectic shopping areas. The trail runs from...
Corson's Inlet Rail-Trail begins at the parking lot off County 619 (by the bridge) in Corson's Inlet State Park and runs for a short distance across the upper dunes above the beach. There are plans to...
The St. Michaels Nature Trail skirts the western edge of the scenic town of St. Michaels, Maryland, which was built on the site of a 17th century Anglican church that eventually lent the settlement...
The Seaside Nature Trail in Cape Henlopen State Park takes visitors to the Seaside Nature Center around a nearly 1-mile rustic loop. A short stretch at the trail's northernmost point runs on a beach...
This community trail begins at the intersection of Main and Pearl streets in the town of Port Norris, near the mouth of the Maurice River. It connects Port Norris with Bivalve. At one time the area...
The Michael Castle Trail offers a scenic 12-mile route along the north shore of the Chesapeake and Delaware Canal in northern Delaware. The trail is named after the former governor and US...
Ocean City Bike Path offers a short, paved route through the center of Ocean City and allows visitors a glimpse into the history of this interesting seaside town. The trail parallels Haven Avenue...
The Seahorse Trail runs primarily along the western edge of Holts Landing State Park. The trail provides access to the park’s campgrounds on its trek through dense forest. Connections to the...
As you walk along the Elephant Swamp Trail, it’s easy to see where it picked up the swamp part of its name. As for the rest, legend has it that in the late 1800s, an elephant got loose in the swamp...
The Marshyhope Creek is a 37-mile tributary of the Nanticoke River running from Delaware to Maryland. One of the towns it passes through is Federalsburg, Maryland, where a 2.5-mile multiuse greenway...
The Killens Pond Bike Trail provides non-motorized access from US 13 to Killens Pond State Park. The short trail parallels Killens Pond Road before turning south into the park along its main access...
The Woodbine Railroad Trail occupies the right-of-way of a former Pennsylvania and Reading Railroad line. The paved pathway traverses Woodbine as it parallels Dehirsch Avenue; a wide grassy median...
Corson's Inlet Rail-Trail begins at the parking lot off County 619 (by the bridge) in Corson's Inlet State Park and runs for a short distance across the upper dunes above the beach. There are plans to...
This beautiful, pine-studded rail-trail winds through Cape Henlopen State Park next to wetlands and farmland, offering a break from the nearby beaches and eclectic shopping areas. The trail runs from...
The Gordons Pond Trail is located in Cape Henlopen State Park, where it skirts the western side of Gordons Pond, a 900-acre salt water lagoon. The finely crushed gravel pathway winds through coastal...
Along New Jersey's coast, a pathway atop a concrete sea wall provides a popular place for North Wildwood residents and visitors to enjoy ocean views. Beginning near 2nd Avenue and John F. Kennedy...
The Bike Loop in Cape Henlopen State Park is a nearly 3.5-mile paved trail through the scenic park. The loop offers various branches that lead off into the marshes with wide vistas of the Atlantic...
The Loblolly Trail in Trap Pond State Park loops around the perimeter of the 90-acre Trap Pond. The trail winds through hardwood forests, crosses a scenic dam at Raccoon Pond and travels over...
The Wayne Gilchrest Trail, which opened on Earth Day in 2012, runs along the southern edge of the historic Maryland Eastern Shore community of Chestertown. The trail connects Washington College to the...
The Swamp Forest Trail loops through Lums Pond State Park on a packed earth surface that accommodates hikers and cyclists. The trail is the shorter of two loops; the Little Jersey Trail runs closer to...
Cape May’s 8.9-mile Middle Township Bike Path and 2.7-mile Cold Spring Bike Path were fully connected in summer 2017. Riders can begin their journey at US 9/Sandman Boulevard in Lower Township across...
Redden State Forest, located just north of Georgetown in Sussex County, offers more than 44 miles of trails for hiking, mountain biking, birdwatching and hunting on several thousand acres. The most...
The Mispillion River Greenway runs through historic downtown Milford on both sides of the Mispillion River. The greenway, which is surfaced primarily with brick and concrete, provides scenic views of...
Maryland's Cross Island Trail spans Kent Island, east to west, in Queen Anne's County, providing multiple points of access to everything from libraries and schools to ball fields and the waterfront....
Have not ridden the Cross Island Trail in a couple of weeks, but drove by it on the way back home from Delaware today. The expansion which begins at the Kent Narrows near Harris' Crab House and ends at Long Point Park is complete and people were walking and riding this section. Beautifully done!
Enjoyed a bike ride from Tall Pines campground all the way to Lewes for lunch! What a gem!
Finally rode it this weekend and loved it. It's nice and flat and was not crazy crowded for a Sunday morning. It hooks right into the Junction Breakwater so you can really get a nice workout between the different routes. The trail now ends at Cool Spring. However, once it is completed to Georgetown, DE it is going to a great addition to Sussex County.
Pros: Beautiful scenery! There are huge farms, pretty sunflowers, and interesting houses. I think I passed by an alpaca and saw a couple of horses and cows as well. There were a lot of dragonflies and butterflies in the air. I biked in 90 degrees weather but the land was vast and it made the weather feel more cool/clear.
Cons: Be careful when you are riding your bike on the road because the speed limit goes up to 50 mph for the cars. I always slow down when I hear a car coming up behind me, but it's always better to be safe than sorry!
Overall experience: Out of the three bike routes I took so far, this area had the most beautiful scenery. As a beginner, I didn't have any trouble navigating the area. I do have to say to not wander off too much because some of the driveways of the homes in the field look like off-bike routes. Don't get confused and stay on the road!
My wife and I rode our tandem from Biddle Point westward to Chesapeake City, where the paved trail connects with local streets. The Michael Castle Trail changes name to the Ben Cardin Trail when you cross into Maryland. There are a couple of hairpin turns, so be aware. The marina are at the inlet near Lums Pond SP is a little tricky to navigate the first time through, but the traffic is low (we rode on a weekday afternoon).
There isn't any shade where the trail runs adjacent to the canal (except where bridges cast shadows), but the few areas where it shifts away from the canal do have tree cover. Bring plenty of water if it's a hot day. We didn't see any place to get water along the trail. We passed 2 other trailheads and they did have restrooms, but they are the waterless type.
Terrain is flat except where the trail moves away from the canal - it becomes slightly hilly.
Overall, it is a great ride.
DELDOT has converted the rail line along Cape Henlopen Dr to a paved path. It extends 1.5 miles from the State Park Entrance to American Legion Drive in Lewes.
The parks at both ends of the trail where the parking lots are located also have fishing piers and charge $10 to park. I couldn't find any decent, free parking so I went to the Cross Island trail.
My husband and I rode this trail today. It was the 1st warm humid day of this year. The trail is not a rail trail. It’s paved and has some uphill sections. It’s in very good condition and we even seen a huge river otter near the route 1 bridge. The closer we got to Delaware city the more osprey we seen too. There isn’t much shade, and along the canal there’s none. I recommend this trail. There are plenty of restrooms and benches on the east side of the route 896 bridge.
For those of you who like this trail, I have good news. They are adding a 1.5 mile extension to the east end of the trail at the Kent narrows bridge. This extension is almost all made of bridge/boardwalk but it is beautiful and runs over the water through wetlands giving a great view of the water. It is supposed to be finished sometime in may. They must have spend several million to add this extension. Can't wait to ride it, will make the trail total distance now about 6 miles.
Little change in grade. Easy to get to - parking available at Wilmer Park. Not too busy for a run or bike ride.
This trail is wonderful in fall, beautiful foliage.
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