Best Trails of Delaware

This list represents the most popular trails in Delaware (learn more about Top Trails). Use this list to plan your next Delaware outdoor trip. Select a state and/or activity below to find even more top trails.

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#1. Brandywine Creek State Park


The lovely Brandywine Creek weaves its way through Chester County, Pennsylvania, and Delaware to join the Delaware River. Along the way the creek has created a valley of stunning natural beauty. Rolli…
From the guidebook "Mountain Biking the Greater Philadelphia Area"
Wilmington, DE - Mountain Biking - 14 miles    Best Trail in DE - Click to view allBestMountain Biking Trail - Click to view all (About Top Trails)
Published by Falcon Publishing

#2. CRABS Challenge


Smell the salty air and feel the seashore breezes as the Come Ride Around the Bays of Sussex (CRABS) Challenge take you on a scenic tour of the bays of Sussex County. You will see some of Delaware's…
From the guidebook "Best Bike Rides in Delaware, Maryland, Virginia, Washington, D.C., & West Virginia"
Rehoboth Beach, DE - Road Biking - 64 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#3. Middle Run Natural Area


As you ride through the park, you'll appreciate the well-marked and well-maintained trails, as well as the handy wooden footbridges. You can thank New Castle County and a number of private local group…
From the guidebook "Mountain Biking the Greater Philadelphia Area"
Newark, DE - Mountain Biking - 7.1 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by Falcon Publishing

#4. Iron Hill Park


Once the site of a large mining operation, Iron Hill Park's334 acres now lie alongside the hustle and bustle of Interstate 95. Many of the old mining pits now offer mountain bikers trails that are lac…
From the guidebook "Mountain Biking the Greater Philadelphia Area"
Newark, DE - Mountain Biking - 15 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by Falcon Publishing

#5. Swamp Forest Trail, Lums Pond State Park


A long but easy hike through the woods around Delaware’s largest freshwater pond. Delaware’s largest freshwater pond, Lums Pond, was created in the early 1800s when St. Georges Creek was impounded to…
From the guidebook "Hiking Maryland & Delaware"
Newark, DE - Hiking - 7.5 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by Falcon Publishing

#6. Delaware-Pennsylvania Hill-Climbing Cruise


This hilly, challenging ride along less traveled roads offers lovely forest and wooded area scenery, with many old homes with lots of historical character. You'll wander on backroads that the develop…
From the guidebook "Best Bike Rides in Delaware, Maryland, Virginia, Washington, D.C., & West Virginia"
Wooddale, DE - Road Biking - 26.7 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#7. Whitetail Trail, White Clay Creek State Park


A hike on the rolling hills of Delaware’s piedmont through meadows, old fields, and impressive woodlands. One of several sections of White Clay Creek State Park, the Walter S. Carpenter Recreation Ar…
From the guidebook "Hiking Maryland & Delaware"
Newark, DE - Hiking - 3 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by Falcon Publishing

#8. Creek Road Trail, Brandywine Creek State Park


Alternating long views and close contact with Brandywine Creek along Creek Road Trail, which here aligns with the Northern Delaware Greenway, the hike includes an interlude above the scenic Rocky Run…
From the guidebook "Hiking Maryland & Delaware"
Wilmington, DE - Hiking - 2.8 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by Falcon Publishing

#9. Fair Hill Natural Resources Management Area


Located in the northeast corner of Cecil County, Maryland, the Fair Hill Natural Resources Management Area covers 5,622 acres of gentle rolling hillsides, lush forests, wandering streams, and fertile…
From the guidebook "Mountain Biking the Greater Philadelphia Area"
Newark, DE - Mountain Biking - 8 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by Falcon Publishing

#10. Two-State Breakfast Cruise


This route from Newark, Delaware to Chesapeake City, Maryland, has long been a popular "breakfast" ride with the White Clay Bicycle Club (WCBC), headquartered in Wilmington, Delaware. The destination…
From the guidebook "Best Bike Rides in Delaware, Maryland, Virginia, Washington, D.C., & West Virginia"
Newark, DE - Road Biking - 48 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#11. Killens Pond Loop, Killens Pond State Park


A walk around an eighteenth-century millpond through diverse wetland and upland forests. Set in the farm country of central Delaware, Killens Pond State Park straddles the boundary between southern a…
From the guidebook "Hiking Maryland & Delaware"
Frederica, DE - Hiking - 3.2 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by Falcon Publishing

#12. Junction and Breakwater Trail, Cape Henlopen State Park


This hike passes through scenic Holland Glade, highlighted by a scenic overlook on a wooden bridge with views of marshland and the ocean in the distance. It follows a wide graded trail through coastal…
From the guidebook "Hiking Maryland & Delaware"
Lewes, DE - Hiking - 6.4 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by Falcon Publishing

#13. Inn-to-Inn Triangle Three-Day Ramble


Nestled between Chesapeake Bay tributaries and the Atlantic Ocean lies the gentle, scenic coastal plain of lower Delaware-terrain ideal for cycling at any level of experience. Although strong riders…
From the guidebook "Best Bike Rides in Delaware, Maryland, Virginia, Washington, D.C., & West Virginia"
Laurel, DE - Road Biking - 98.2 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#14. Amish Country Challenge


This ride will take you past picturesque farms, green meadows, and quaint old buildings. Unlike other rides, this will also take you past slow-moving horse-drawn buggies and traditional Amish women t…
From the guidebook "Best Bike Rides in Delaware, Maryland, Virginia, Washington, D.C., & West Virginia"
Dover, DE - Road Biking - 61.51 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#15. Burton's Island Loop, Delaware Seashore State Park


An easy, interpretive hike on boardwalks, sand, and soft upland soil through salt marsh and coastal forest. With good facilities near the trailhead and interesting options, a walk on the nature trail…
From the guidebook "Hiking Maryland & Delaware"
Rehoboth Beach, DE - Hiking - 1.5 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by Falcon Publishing

#16. Bombay Hook National Wildlife Refuge Loop


A circuit hike on the dirt roads of a Delaware Bay wildlife refuge. This is an especially rewarding hike for those interested in watching migrating shorebirds and waterfowl, nesting bald eagles, and r…
From the guidebook "Hiking Maryland & Delaware"
Dover, DE - Hiking - 8.3 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by Falcon Publishing

#17. Redden State Forest Loop, Delaware Seashore State Park


An easy walk through a tract of Delaware’s largest state forest in the heart of loblolly pine country. A good hike for exploring the natural and cultural history of a relatively new wild and managed f…
From the guidebook "Hiking Maryland & Delaware"
Georgetown, DE - Hiking - 5 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by Falcon Publishing

#18. Brandywine Valley Area, PA & DE


For more than 300 years—from the time of William Penn—people have sought refuge and renewal in the Brandywine Valley. This bucolic landscape on either side of the Brandywine River in Pennsylvania and…
From the guidebook "Great Family Vacations: Northeast"
Wilmington, DE - Hiking Best Trail in DE - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#19. Gordons Pond, Cape Henlopen State Park


This walk weaves around a mile-long tidal pond and ends at the ocean, offering arm’s-length views of more than a dozen species of shorebirds. Crouching near the great tidal pool known as Gordons Pond,…
From the guidebook "Hiking Maryland & Delaware"
Rehoboth, DE - Hiking - 4 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by Falcon Publishing

#20. Southern Delaware Heritage Challenge


Few activities, cycling or otherwise, showcase the people, places, and culture of southern Delaware as comprehensively and enjoyably as this ride. The flat, easy 106-mile ride takes you by the area's…
From the guidebook "Best Bike Rides in Delaware, Maryland, Virginia, Washington, D.C., & West Virginia"
Bridgeville, DE - Road Biking - 115.8 miles    Best Trail in DE - Click to view all (About Top Trails)
Published by The Globe Pequot Press