Best Road Biking in Maryland

Trying to find the best road biking in Maryland? Bivy has great hiking, biking, paddling, climbing, skiing, riding and more, with hand-curated trail maps, as well as detailed driving directions.

1

Virginia, Waynesboro

02 :44 hrs
27.6 mi
109.79724 ft
Hard

This ride will take you through the amazing Shenandoah Valley. You will encounter a long gradual climb out of the city, which can be challenging for the beginner rider. After you pass the climb, there will be a gradual descent. There will be short stretches of busy streets with heavier traffic throughout the ride. Plan on rolling hills for long stretches.

2

Virginia, Rockbridge County

02 :02 hrs
20.5 mi
96.36255 ft
Hard

This is a good route for beginners. The roads are all paved and in good condition. The ride is considered an out and back excursion with the exception of the small loop in Goshen. It is located in what is considered the most scenic part of Virginia. The way home from Goshen is easier than the beginning of a ride.

3

Maryland, Berlin

10 :02 hrs
100.6 mi
12.4915085 ft
Extreme

This is a great 100-mile cycling route through Maryland’s only seaside county, featuring great rural landscapes, curious and historic towns and villages, spectacular waterfronts, abundant travel amenities and more nature than one could possibly imagine. This trip covers a lot of ground and passes through many quaint, historic towns, winds through forest and farm country, and crosses many rivers including the Pocomoke and Nassawango Rivers. The sweeping landscaping offers breathtaking scenery and there are many beautiful points of interest along the way. An alteration of this route is mapped which includes Assateague Island and is called, “Inn to Inn on the Lower Shore.”

4

Maryland, Easton

08 :48 hrs
88.1 mi
4.669523 ft
Extreme

Delmarva is a long peninsula encompassing Delaware, the eastern shore of Maryland, and part of Virginia and lies between the Chesapeake Bay and the Atlantic Ocean. Much of it consists of commercial farmland and is an ideal place for cycling due to the little-traveled country roads, gently rolling coastal plains and farm fields and pristine views of the sparkling water. In addition, there are several quaint towns, antiques shops, superb seafood restaurants, and a nautical museum. This ride incorporates a short ferry ride on the oldest continuously operating ferry in the United States. There are several other roads to ride and further explore the beautiful countryside and obtain different water views. The Oxford-Bellevue Ferry is open 7 days a week and runs every 15-20 minutes from 9:00 a.m. to sunset but exact times and dates may vary so check on the schedule before making this trip.

5

Maryland, Easton

02 :13 hrs
22.2 mi
4.529985 ft
Hard

Delmarva is a long peninsula encompassing Delaware, the eastern shore of Maryland, and part of Virginia and lies between the Chesapeake Bay and the Atlantic Ocean. Much of it consists of commercial farmland and is an ideal place for cycling due to the little-traveled country roads, gently rolling coastal plains and farm fields and pristine views of the sparkling water. In addition, there are several quaint towns, antiques shops, superb seafood restaurants, and a nautical museum. This ride incorporates a short ferry ride on the oldest continuously operating ferry in the United States. There are several other roads to ride and further explore the beautiful countryside and obtain different water views. The Oxford-Bellevue Ferry is open 7 days a week and runs every 15-20 minutes from 9:00 a.m. to sunset but exact times and dates may vary so check on the schedule before making this trip.

6

Maryland, Harford County

00 :28 hrs
2.4 mi
3.6318684 ft
Easy

This trail is located in the Susquehanna State Park which is recognized for its hiking and biking trails, camping, rock outcroppings, boating, and much more. This is a beautiful paved trail along the stunning Susquehanna River that flows majestically by. This is a rail-trail that follows the corridor built in 1926 by the Philadelphia Electric Company to transport materials from Havre d’Grace to the Conowingo Dam. From the trail you will enjoy wooded wetlands, songbirds, wildflowers, and a dense canopy overhead, shading the trail while still allowing frequent river views.

7

Maryland, Washington County

02 :11 hrs
21.8 mi
30.56549 ft
Hard

The Western Maryland Rail Trail is a paved route that is packed with history and the trail will take you through several eras of American history. You can access the trail from many points and the main trailhead is in the town of Hancock, but this route extends the entire length of the trail from Fort Frederick State Park to Pearre Road. You will parallel the C & O Canal and its unpaved towpath, which was used to transport coal from Cumberland to Georgetown. The trail has magnificent views of the Potomac River, large rock outcroppings, the ruins of the Round Top Center Mill, historical markers for Little Pool and Park head cemeteries, and wildlife such as deer and wild turkey.

8

Maryland, Snow Hill

08 :59 hrs
89.9 mi
12.570446 ft
Extreme

The lower Eastern Shore of Maryland is a cyclist’s dream as it is almost totally flat, and has great scenery, much preserved history, and bicycle-friendly inns, many of which have joined together to provide special services to cyclists. This tour covers a lot of ground as it leaves Snow Hill, swoops down to the public landing on Chincoteague Bay, leads through chicken-farm country to historic Berlin, continues to Assateague Island where wild ponies graze, and visits Berlin’s restored Atlantic Hotel, cross the Pocomoke River and Nassawango Creek, visit an old iron furnace and restored town, and end back in Snow Hill. This tour is inspired by Viewtrail 100, a well-marked 100-mile tour mapped out by Worcester County.

9

Maryland, Wicomico County

06 :18 hrs
63 mi
11.461307 ft
Extreme

Nautical history buffs ought to especially enjoy this ride, as its destination, Deal Island in the Tangier Sound, is the home of one of the last remaining skipjack fleets. Skipjacks are sailing vessels that are not motorized and in the nineteenth century were the primary way fishermen tongued for oysters. On this ride you will also enjoy cycling through miles of farmland, the tidal marshland of the Deal Island Wildlife Management Area, and the historic town of Princess Anne which is home to the 200-year old Washing Hotel. The terrain is mostly flat but the land is exposed and there is a significant prevailing wind from the west. This route is marked in orange arrows numbered 62 by the Salisbury State University Cycling Club.

10

Delaware, Dover

04 :58 hrs
49.8 mi
14.178757 ft
Extreme

This is a great ride through a rural area that will take you past picturesque farms, green meadows, and quaint old buildings. It will also take you past slow-moving horse-drawn buggies and traditional Amish women tending their gardens. The route follows lightly traveled back roads from the historic town of Dover into these vast and scenic outlying farmlands. The terrain is extremely flat with plenty of places to rest.

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