5.0
(8)
146
riders
20
rides
Touring cycling in Garrett County offers routes through the mountainous terrain of Western Maryland, characterized by dense forests, rolling hills, and the expansive Deep Creek Lake. The region's topography includes varied elevations, providing both challenging climbs and more gradual paths. Many routes follow former railway lines, offering relatively flat sections through scenic valleys. The landscape is shaped by the Appalachian foothills, featuring a mix of natural waterways and wooded areas.
Last updated: July 29, 2026
13
riders
24.9km
01:57
350m
350m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
13
riders
12.1km
01:11
200m
200m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Sign up for free
9
riders
23.4km
02:13
340m
340m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(2)
5
riders
80.7km
05:42
1,570m
1,570m
The Chocolate Drop Hill loop from McHenry offers a truly demanding touring cycling experience, immersing you in the diverse natural beauty of McHenry County. As you pedal, you'll traverse landscapes ranging from open prairies to dense oak savannas and wetlands, with the potential for scenic stretches along the Fox River or around Lake Defiance, similar to those found in Moraine Hills State Park. This route is designed for cyclists who appreciate a significant physical challenge and the changing scenery that comes with it.
Prepare for a substantial day out, as this difficult route covers 50.1 miles (80.7 km) with an impressive 5155 feet (1571 metres) of elevation gain, typically taking around 5 hours and 42 minutes to complete. While specific parking for this exact loop isn't detailed, general access points for cycling in the McHenry area are available, often near parks. An early start is recommended, especially on weekends, to avoid potential high foot traffic on shared paths and to allow ample time for the full duration of the ride.
This route stands out as one of the more challenging touring cycling options in the region, pushing your limits across varied terrain. McHenry County is known for its extensive trail system, including the Prairie Trail, which connects many of these natural areas. The diverse environment, shaped by glacial activity, provides a rich backdrop for your ride, offering glimpses of local wildlife and a true sense of exploration away from urban hustle.
2
riders
40.4km
02:34
470m
470m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
1
riders
35.8km
02:18
430m
430m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
riders
38.0km
02:27
490m
490m
If you're seeking a challenging ride that truly tests your legs, the "Bike loop from Oakland" delivers a difficult 23.6 miles (38.0 km) of touring cycling. This route plunges you into the East Bay hills, moving beyond the flat waterfront paths to offer significant climbs and descents. Expect to navigate varied terrain, likely passing through wooded areas similar to Redwood Regional Park, where the effort of ascending is consistently rewarded with expansive bay and city views.
Planning for this 2 hour and 26 minute adventure means preparing for a substantial workout, with 1605 feet (489 metres) of elevation gain. While specific access points aren't detailed, many challenging Oakland cycling routes start from regional parks, so consider public transport to a suitable hub or look for parking options near park entrances. Always ensure your bike is in top condition and carry ample water, especially if you tackle this loop during warmer months.
This particular loop stands out among Oakland cycling routes for its focus on elevation and difficulty, catering to those who prefer a rigorous experience over a leisurely cruise. It's a prime example of the more advanced bike touring trails available in the region, offering a different perspective of the Bay Area's natural beauty and urban landscape compared to the popular cycling trails along the shoreline. It's a great option if you're looking to push your limits and explore the less crowded, hilly side of Oakland's cycling scene.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
Popular around Garrett County

Cycling in Savage River State Forest

Cycling around Finzel
Cycling in Deep Creek Lake State Park

Cycling in Fork Run Recreation Area

Cycling in Potomac/Garrett State Forest

Cycling in Potomac State Forest Backbone Area

Cycling in Garrett State Forest Piney Mountain, Snaggy Mountain, Hutton Areas

Cycling around Swanton
Hiking in Garrett County
Road Cycling Routes in Garrett County
The Mason-Dixon Line Monument marks the historic boundary between the states of Maryland and Pennsylvania. Today, it is a scenic rest stop for hikers, featuring a granite obelisk, engraved blocks spelling "Mason & Dixon," and a replica of the surveyors' 66-foot chain. It is a great photo opportunity and Easily a must-see for history buffs.
1
0
Congratulations! You've reached the highest point in the Great Allegheny Passage, which runs from Pittsburgh, Pennsylvania to Cumberland, Maryland. The Eastern Continental Divide marks a stark divide between two watersheds: To your east, the waterways drain (eventually) into the Atlantic Ocean. The waters to your west funnel toward the Gulf of Mexico.
0
0
The Big Savage Tunnel is one of the highlights of the GAP. The 3,291-foot tunnel was refurbished for bike use in 2003 and has a modern lighting system. On the eastern end of the tunnel there is a great viewpoint and picnic tables.
2
0
The Borden Tunnel is one of the signature tunnels along the GAP. It is almost 1000-feet long and is equipped with motion-detected lighting. It is considered one of the most tranquil places on the trail.
0
0
Congratulations! You've reached the highest point in the Great Allegheny Passage, which runs from Pittsburgh, Pennsylvania to Cumberland, Maryland. The Eastern Continental Divide marks a stark divide between two watersheds: To your east, the waterways drain (eventually) into the Atlantic Ocean. The waters to your west funnel toward the Gulf of Mexico.
1
0
The aviary at Deep Creek Lake State Park shelters nine birds of prey. This aviary is part of the Scales & Tales program, whose goal is environmental education. The birds arrive here injured or hand-raised and cannot survive in the wild. The birds are well taken care of by workers and volunteers.
0
0
Deep Creek Lake Sand Beach is the perfect spot for relaxation and recreation. Visitors enjoy canoeing and kayaking in well-maintained facilities, including clean bathrooms, playground areas, and numerous picnic tables with metal grills. Rental options for kayaks and paddle boards are available, and the sandy beach area has a few shade trees. The water is great for swimming and sunbathing. There are restrooms on site with showers.
0
0
Originally a railway tunnel, the Big Savage Tunnel was refurbished to serve cyclists and hikers in 2003. It offers great protection from the weather and has arched, portal doors that might just make you feel like you're about to enter the Mines of Moria.
0
0
Garrett County offers a diverse selection of over 20 touring cycling routes. These routes cater to various skill levels, with a mix of moderate and difficult options through the region's mountainous terrain.
While Garrett County's touring cycling routes are generally rated as moderate to difficult due to the mountainous terrain and elevation changes, some sections of former railway lines offer more gradual paths. For a moderate option that provides scenic views and access to recreational areas, consider the Deep Creek Lake Sand Beach loop from Deep Creek Lake State Park, which is 10 miles long.
You can expect varied terrain, from dense forests and rolling hills to paths along the expansive Deep Creek Lake. Many routes utilize former railway lines, offering relatively flat sections through scenic valleys, while others feature challenging climbs characteristic of the Appalachian foothills.
Garrett County's routes often pass by significant natural and historical points. You can explore areas like Deep Creek Lake State Park, which includes the Deep Creek Lake State Park Aviary. Some routes also pass historical markers, such as those found on the Meyersdale Visitors Center – Mason-Dixon Line Monument loop from WMSR- Frostburg.
Yes, many routes in Garrett County are designed as loops, allowing you to start and end at the same point. Examples include the Deep Creek Lake Sand Beach loop from Deep Creek Lake State Park, the Frostburg Trailhead – Helmstetter’s Curve loop from WMSR- Frostburg, and the Fike Hill loop from Mountain Dale.
The best time for touring cycling in Garrett County is typically from late spring through early fall (May to October). During these months, the weather is generally mild, and the natural scenery, from lush forests to vibrant fall foliage, is at its peak. Always check local weather conditions before heading out, especially in the mountainous areas.
The touring cycling routes in Garrett County are highly rated by the komoot community, with an average score of 5.0 stars from over 5 reviews. Cyclists often praise the diverse terrain, from forested mountains to lakefront paths, and the unique experience of riding along historic railway trails.
Experienced touring cyclists will find several challenging routes in Garrett County. For instance, the Chocolate Drop Hill loop from McHenry is a difficult 50-mile route with significant elevation changes. Another demanding option is the Frostburg Trailhead – Helmstetter’s Curve loop from WMSR- Frostburg, which spans over 50 miles through forested areas.
Many touring cycling routes in Garrett County originate from state parks, trailheads, or visitor centers, which typically offer designated parking facilities. For example, routes around Deep Creek Lake often start near Deep Creek Lake State Park, and railway trail routes may have parking at their respective trailheads like the Frostburg Trailhead.
Yes, several touring cycling routes provide stunning views of Deep Creek Lake. The Deep Creek Lake loop from Deep Creek Lake is a moderate 22-mile route that circles the lake, offering continuous scenic vistas. Another option is the Deep Creek Lake State Park – Deep Creek Lake Sand Beach loop from Deep Creek Lake State Park, a more challenging 26-mile ride with lake views.
Given Garrett County's mountainous landscape, touring cycling routes often involve significant elevation changes. For example, the Mason-Dixon Line Monument – Big Savage Tunnel loop from Saint Mary Catholic Church includes over 1,500 feet of ascent, while the Chocolate Drop Hill loop from McHenry features over 5,000 feet of climbing, making for challenging rides.


Check out more Cycling routes throughout Garrett County below and find the perfect route in your destination.
Browse the best Cycling routes in other regions.