4.7
(7)
121
riders
32
rides
Road cycling routes around Friendship offer diverse landscapes across two distinct regions: Wisconsin and near Maryland's Chesapeake Bay. The Maryland area features flat terrain with waterfront views along Herring Bay, a large body of water on the western shore of Chesapeake Bay. In Wisconsin, the region is characterized by peaceful small-town settings, mixed forests, and serene lakes. Cyclists can expect routes that traverse woodlands, scenic farmland, and areas with natural bluffs.
Last updated: July 12, 2026
5.0
(1)
9
riders
63.5km
02:43
410m
410m
Embark on the Bay to River Historic Route for a moderate road cycling adventure. This route spans 39.5 miles (63.5 km) and features a total elevation gain of 1339 feetโฆ
4.0
(2)
12
riders
77.3km
03:14
450m
450m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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4.0
(1)
11
riders
49.8km
02:04
300m
300m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
3
riders
71.6km
03:01
550m
550m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
10
riders
43.4km
01:47
260m
260m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Popular around Friendship
This is a small, picturesque beach community, with a nature center, a sunrise garden, and a small beach.
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A vast bay on the western shore of Chesapeake Bay, the largest estuary in the US. You can find over 300 species of fish, shellfish and crabs as well as ospreys, peregrine falcons and bald eagles here. The waters are also an important nursery area for sharks on the east coast โ hammerhead sharks, basking sharks and tiger sharks often visit. Dolphins and whales can be seen here too. It's a paradise for nature lovers.
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Tracy's Creek is one of the three waterways that converge in Herring Creek. It runs for approximately one mile, starting from the S.R. 256 Bridge and flowing towards Herrington Harbour North. This waterway offers a great opportunity to see many pleasure crafts harbored in the marina as you pass by.
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A lovely beach in North Beach open from 8 am until 8 pm. A great place to relax and enjoy the sea close to town. Entrance is free for residents if you have a beach pass or $25 for non-resident adults.
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A vast bay on the western shore of Chesapeake Bay, the largest estuary in the US. You can find over 300 species of fish, shellfish and crabs as well as ospreys, peregrine falcons and bald eagles here. The waters are also an important nursery area for sharks on the east coast โ hammerhead sharks, basking sharks and tiger sharks often visit. Dolphins and whales can be seen here too. It's a paradise for nature lovers.
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There are over 25 road cycling routes around Friendship, offering a variety of experiences. You'll find options ranging from easy rides to more moderate challenges, with 12 easy routes and 15 moderate routes to explore.
Road cycling around Friendship offers diverse landscapes depending on the region. In Wisconsin, you'll find peaceful small-town settings, mixed forests, and serene lakes like Friendship Lake and Castle Rock Lake. Near Maryland's Chesapeake Bay, routes feature flat terrain with extensive waterfront views along Herring Bay, passing through coastal communities and offering glimpses of abundant wildlife.
Yes, both regions offer scenic points. In Wisconsin, the striking 300-foot Roche-a-Cri Mound in Roche-a-Cri State Park provides panoramic views. The park also features mixed forests and prairie restorations. Near Maryland's Herring Bay, many routes offer picturesque waterfront views, where you can observe various birds and marine life.
Yes, there are 12 easy road cycling routes around Friendship. These routes are generally shorter and have less elevation gain, making them ideal for those new to road cycling or looking for a relaxed ride. An example is the Herring Bay โ Tracys Creek loop from North Beach, which is rated as easy.
For more experienced riders seeking longer distances, routes like the Herring Bay โ North Beach loop from Tracys Landing cover over 38 miles (62 km) with moderate elevation changes. Another option is the Tracys Creek โ Herring Bay loop from Deale, which is nearly 37 miles (59 km) long.
Yes, the region offers family-friendly options, particularly in Wisconsin where the Friendship State Trail provides a significant draw for cyclists. This trail features both crushed limestone and paved surfaces through woodlands and scenic farmland, suitable for a leisurely family ride. Look for the 'easy' rated routes on komoot for suitable options.
Many of the road cycling routes around Friendship are loops, allowing you to start and end at the same point. Examples include the popular Herring Bay โ Shady Side to Galesville Route loop from Tracys Landing and the Shady Side to Galesville Route loop from Tracys Landing.
The best time for road cycling in Friendship generally spans from spring through fall. During these seasons, the weather is typically mild, offering pleasant conditions for exploring the diverse landscapes. Summer can be warm, especially in Maryland, but the waterfront routes often provide a refreshing breeze. Always check local weather forecasts before heading out.
Parking availability varies by location. For routes near Maryland's Herring Bay, you can often find parking in coastal communities like Tracys Landing or North Beach, which serve as common starting points. In Wisconsin, state parks like Roche-a-Cri State Park and trailheads for the Friendship State Trail typically offer designated parking areas.
Yes, especially along routes that pass through small towns and coastal communities. Near Maryland's Herring Bay, routes often go through areas with local eateries and cafes where you can refuel. In Wisconsin, the small-town atmosphere means you'll find local establishments in communities along or near the cycling paths.
The road cycling routes around Friendship are highly rated by the komoot community, with an average score of 4.75 stars from over 10 reviews. Cyclists often praise the diverse scenery, from the peaceful woodlands and lakes in Wisconsin to the extensive waterfront views along Maryland's Herring Bay. The variety of routes suitable for different skill levels is also frequently highlighted.


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