Essex, MD Snowmobiling Trails and Maps

1413 Reviews

Looking for the best Snowmobiling trails around Essex?

Find the top rated snowmobiling trails in Essex, whether you're looking for an easy short snowmobiling trail or a long snowmobiling trail, you'll find what you're looking for. Click on a snowmobiling trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
Surfaces
Type

Great American Rail-Trail

3743.9 mi
State: DC, IA, ID, IL, IN, MD, MT, NE, OH, PA, WA, WV, WY
Asphalt, Concrete, Crushed Stone

Kent Island South Trail

5.8 mi
State: MD
Asphalt
Trail Image Trail Name States Length Surface Rating
Note: This developing route is not yet fully contiguous – it is just over 50% complete. Please refer to the Trail Map for more information on the existing sections of trail, as well as the online...
DC, IA, ID, IL, IN, MD, MT, NE, OH, PA, WA, WV, WY 3743.9 mi Asphalt, Concrete, Crushed Stone
The Kent Island South Trail is one of two popular recreational trails on Maryland’s Kent Island, the largest island in the Chesapeake Bay (the other is the Cross Island Trail). The trail runs parallel...
MD 5.8 mi Asphalt

Recent Trail Reviews

Jones Falls Trail

Disappointing Trail

July, 2025 by jims216

I kept hearing how beautiful this "trail" was. Most of the "trail" was city streets even before you get in to Baltimore. It was also poorly marked. Keep a GPS handy, or just give up on the trail and ride through whatever Baltimore streets you feel like riding.

It does take you past the Baltimore Zoo which was nice. It also takes you right in to Inner Harbor which is also a good place to hang out for a bit.

Wayne Gilchrest Trail

Small Town Trail With Regional Potential

July, 2025 by jmcginnis12@gmail.com

Stretching for more than 2 miles across Chestertown on MD's Eastern Shore, the Wayne Gilchrest Trail is a scenic greenway that has the potential to connect to more communities.
Like many town-based trails, the paved, multi-use path allows residents to walk or bike between communities with minimal street crossings. It links Washington College with the north and south sides of town and the southern terminus along Cross Street is just a short distance from the waterfront at Wilmer Park as well as the historic downtown. Also notable is a spur of the trail that branches from the main path on the grounds of an office building and parallels High Street, connecting to the northwest side of town and ending at the former Radcliffe Mill, which has been restored and now houses a restaurant and microbrewery.
The trail also serves as an outdoor museum of sorts and features several sculptures and murals along the route, while the old train station, vintage passenger coaches and caboose at the southern end off Cross Street are a testimony to the rail line that used to run here.
Last, but not least, the lush vegetation that lines most of the trail's route provides a serene atmosphere and is a great place to observe local wildlife. The section from Mill Street south to Cross Street forms a greenbelt between residential communities and the Lawrence Preserve nature area, whose wetlands can be further explored through a network of paths extending from the trail. The ravine that forms the trail's route through the Washington College campus and the embankment on the portion north of Morgnec Road are also notable for their beauty and serenity.
My only caveats with this premier small town trail are the busy crossings on Morgnec Road and High Street, though flashing signal lights that warn motorists when trail users are crossing reduce the danger to a degree and the lack of any direct connection to Washington College. It would also be nice if a separate connector path or sidewalk could be built along Morgnec Road that would link the NW Spur of the trail with the main route on the north side of town so that trail users don't have to use the shoulder of that busy road.
Although currently confined to Chestertown, local officials are exploring plans to extend the Wayne Gilchrest Trail further north along the old RR towards Worton, forming part of a bigger network of greenways on the Eastern Shore.

Torrey C. Brown Rail Trail

Shaded Ride

July, 2025 by larry.adams6094

Rode most of the trail yesterday starting in Railroad, PA on the Heritage Trail and turned around at the old train station in Monkton, MD. Temperature was in the mid-80s, and humidity was high. Because most of the trail was shaded, it was still a great ride. Definitely not a trail for narrow road tires, but still an excellent surface of crushed stone and hard packed dirt. Plenty of restrooms and stops available. Slightly downhill starting in New Freedom, PA into MD for about 6-7 miles and then a typical rail trail of mostly flat and straight sections. Great scenery of wooded areas. Highly recommend for a relaxing ride in the woods.

Accordion

Hanover Trolley Trail

too cool, too short

July, 2025 by sunnybrookusa

Great trail close to my home so I get to ride it as often as I want. I’m looking forward to another leg being completed and hoping it doesn’t take 10 years. I took my 9 year old twin grand sons on it and they love it too.

Anacostia River Trail

well maintained

July, 2025 by bwjcgtc4kb

The trail is 100% paved and takes you along the Anacostia River. I like that this trail has a good mix of city elements and natural beauty. The Kenilworth aquatic gardens are a wonderful stop early in the trail, you get to see a lot of swamp flowers. Later, closer to Dc you are taken up to the Fredrick Douglas memorial bridge. The large white arches of the bridge are breathtaking. There are many places to eat diner once you make it to Dc. I stopped at Gordon Ramseys fish and chips. Great trail!

PennDel Trail

Varying conditions throughout

July, 2025 by tnbpptw5x7

Definitely an adventure on a bike. Some parts are smooth; others are pretty rugged. Just be prepared for some rocks. 10mph feels like flying.

Pomeroy and Newark Rail Trail

Neat trail with varying conditions

July, 2025 by tnbpptw5x7

The southern part is paved and easy to follow. The middle section joins with a state park road, and one siding is deceiving. After leaving the state park road, the trail turns to gravel with frequent mud puddles and electrical boxes. Wouldn’t recommend this section to beginners.

James F. Hall Trail

Simple

July, 2025 by tnbpptw5x7

Not much to it. Just paved and easy. The trains do get loud so maybe not the best for small children.

Enola Low Grade Trail

23.5 Miles are Great

July, 2025 by joshua.d.waterman

The Enola Low Grade Trail is a great rail trail for biking and walking. Starting from the Turkey Hill end, the first 6 or so miles are super scenic along the river. Once the trail turns inland it is less scenic but still a very nice ride.

It should be noted that once you reach Hollow Rd east of Quarryville (around mile marker 23 or so), the trail is not particularly bike-friendly and the last mile is so overgrown it's not even really hike-friendly.

The trail is marketed as 29.1 miles, but if you're planning on biking, it is about 23 miles.

Enola Low Grade Trail

Excellent choice for a long, flat ride

June, 2025 by tedreese_tl

“Low Grade” is no exaggeration and this is an excellent trail if you’re looking for a long, flat cruise. As others have commented, the scenic highlights are on the western half of the trail so start at Turkey Hill trailhead if that’s what you’re looking for. Portable toilets at maybe half the trailheads. No easy access to stores/conveniences (except Quarryville) so BYO water and nutrition

Custis Trail

Convenient to DC from Arlington and surrounding areas

June, 2025 by zap26

I have used this trail a few times to commute from the Arlington, VA area into the district. It is convenient but could use a repaving. The paved path is bumpy (It looks like tree roots grew to create the wavy in the path). The first time I rode it I was pulling my dog and the wavy ness of the trail actually broke the bike rack connecting the dog trailer from the bumps. 3 years later from when by rack broke, the path has only gotten more wavy.

This trail is also hilly so you will get a workout. Going from Ballston to DC it was more downhill and rather easy, coming back the hills were somewhat steep. A good workout but not overly difficult.

On a side note: If you are visiting DC, I strongly suggest using the bike trails in DC, around DC, and all the trails in the surrounding areas. Every Smithsonian has bike racks to lock up your bike while visiting the museums. It is a great way to see the monuments, museums, and the mall without miles of walking. Today I first went to Library of Congress (to do some research), then to National African American Museum, and to the Native American Museum. I rode about a mile between the two museums which was much easier than walking.

Chesapeake & Ohio Canal National Historical Park

Simply spectacular

June, 2025 by ethantabor

I just finished a two-day solo tour (Cumberland to Williamsport, Williamsport to DC) and had an incredible experience despite the rain and the tough going over a few stretches. I hear a lot of criticism about the C & O, particularly when compared to the GAP (which I have also done). I appreciate the contrast and hope that the C&O retains its historic character as a more rugged towpath (not a rail trail). That said, the conditions on the east side of Paw Paw and from White’s Ferry to DC were challenging (again, I like the changing surfaces). Highlights: wilderness character, Paw Paw Tunnel, sycamores between Harper’s Ferry and Antietam, Great Falls, Monocacy, Point of Rocks station and the towns.

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