Maryland road guide
The best motorcycle roads in Maryland
The best motorcycle roads in Maryland are in the mountains out west and along the water in the east. Old US 40 over Town Hill, the Georges Creek valley and the long Garrett County grades are the mountain rides, MD 77 and MD 24 are the short twisty escapes from the cities, and MD 213, MD 33 and MD 335 trace the Chesapeake. Here are 15 classics, with the region, why each is worth it, what to watch for and the best season.
- Roads listed
- 15
- Regions
- 3
- Best months
- May to Jun, Sep to Oct
- Check before you go
- MD 511
Before you pick
How to use this list of the best motorcycle roads in Maryland
Maryland doesn't take long to cross, but the riding changes completely from one end to the other. The far west is Appalachian ridge and valley country, with much of Garrett County above 2,000 feet. The middle is rolling Piedmont farmland with a couple of real mountain crossings at Catoctin and South Mountain. The east is flat tidewater, where roads follow creeks, marsh and the bay. Pick the region first, then the road.
The list runs west to east. Mountain roads are best from late spring to mid October, and water roads are best in the shoulder seasons, when the beach crowds are gone. Check MD 511 for closures and incidents before a long day, and see the Maryland riding overview for the state at a glance and the best time to ride in Maryland for month-by-month timing.
Western Maryland
Garrett and Allegany counties: Maryland's mountain roads
- 1. Old US 40 over Town Hill (Scenic 40)Why: West of Hancock, I-68 took the traffic and left the old National Pike as a quiet two-lane that climbs and drops over one ridge after another toward Flintstone. The overlook at Town Hill is the classic stop. Watch for: Steep downhill bends, gravel washed across the road after storms, and deer. Best season: May to October, with foliage in mid October.
- 2. Alternate US 40, Cumberland to GrantsvilleWhy: Alt 40 leaves Cumberland through the Narrows, passes the old toll gate house at La Vale, runs through Frostburg and over the high ridges toward Grantsville, where an early 1800s stone arch bridge over the Casselman River sits in a small state park. Watch for: Fog and sudden cold up high, town traffic in Frostburg, and trucks on the grades. Best season: May to October.
- 3. US 219 through Garrett CountyWhy: The spine of Maryland's highest county, past Deep Creek Lake and through Oakland, with Backbone Mountain, home of the state's high point, to the south. Side roads lead to Swallow Falls State Park and around the lake. Watch for: Boat trailers and lake traffic on summer weekends, deer, and a snow season that starts early and ends late. Best season: Late May to mid October.
- 4. MD 135, Oakland to WesternportWhy: East from Oakland through Mountain Lake Park and Deer Park, then a long, steep descent toward Bloomington and the North Branch of the Potomac. A lot of elevation in a short distance. Watch for: The grade, which heats brakes and carries trucks, and wet leaves in fall. Take the downhill slowly. Best season: May to October.
- 5. MD 36, the Georges Creek valleyWhy: Climbs from Westernport up the Georges Creek valley through old coal towns like Lonaconing and Midland to Frostburg. Pair it with MD 135 for a loop. Watch for: Town speed zones, parked cars and patched pavement. Best season: May to October.
- 6. MD 51 along the PotomacWhy: Runs southeast from Cumberland past Oldtown toward Paw Paw, West Virginia, staying close to the river and the C&O Canal. The canal's Paw Paw Tunnel trailhead near the end makes a good stop. Watch for: Deer, very few services, and debris after high water. Best season: April to October.
Central Maryland
Central Maryland: Catoctin, Antietam and the reservoirs
- 7. MD 77 over Catoctin MountainWhy: Climbs west out of Thurmont beside Big Hunting Creek, between Catoctin Mountain Park and Cunningham Falls State Park, then drops toward Smithsburg. The closest real mountain road to Frederick. Watch for: Damp pavement under the trees, cars pulling out of park lots, and crowds at the falls on nice weekends. Best season: April to June, September to October.
- 8. MD 17 and the Middletown ValleyWhy: Runs north from Brunswick on the Potomac through Burkittsville and Middletown, in the farm valley between Catoctin Mountain and South Mountain. Detour up Gapland Road to Gathland State Park at Crampton's Gap. Watch for: Farm equipment, cyclists, and deer at the field edges. Best season: April to October.
- 9. MD 34 and MD 65 at AntietamWhy: MD 34 from Boonsboro and MD 65 from Hagerstown meet at Sharpsburg beside Antietam National Battlefield. Slow park roads inside, quiet farm roads around it, and the Potomac crossing to Shepherdstown close by. Watch for: Tour traffic and people on foot at the monuments. Best season: April to November.
- 10. MD 24 through Rocks State ParkWhy: North of Bel Air, MD 24 winds through Rocks State Park beside Deer Creek, below the rock outcrop known as the King and Queen Seat. One of the best short rides from Baltimore. Watch for: Tight, blind bends, swimmers and anglers parking along the creek, and wet leaves in fall. Best season: April to October.
- 11. The Prettyboy Reservoir roadsWhy: In northern Baltimore County, the county roads around Prettyboy Reservoir dip down to the water and climb back through the woods. Add Loch Raven on the way home for a half day that never strays far from the city. Watch for: Narrow lanes, short bridges, cyclists and parked cars at trailheads. Best season: April to October.
The bay
The Eastern Shore and Southern Maryland
- 12. MD 213, Chesapeake City to ChestertownWhy: From Elkton, MD 213 crosses the C&D Canal on the high bridge at Chesapeake City, then rolls through farm country and Galena into colonial Chestertown and on to Centreville. Add MD 20 out to Rock Hall. Watch for: Crosswinds on the canal bridge, farm equipment, and slow going in town. Best season: April to June, September to November.
- 13. MD 33 to St. Michaels and Tilghman IslandWhy: From Easton, MD 33 crosses Talbot County's necks of land to St. Michaels and the Chesapeake Bay Maritime Museum, then over the Knapps Narrows drawbridge onto Tilghman Island, with water on both sides near the end. Watch for: Summer weekend crowds in St. Michaels, the drawbridge, and wind. Best season: May to June, September to October.
- 14. MD 335 to Hoopers IslandWhy: South of Cambridge, MD 335 runs through the marsh country around Blackwater National Wildlife Refuge and past the Harriet Tubman Underground Railroad visitor center near Church Creek, out to the low bridges of Hoopers Island. Big skies, eagles and almost no traffic. Watch for: Water right beside the road, flooding at high tide and in storms, and biting flies in summer. Best season: April to May, September to November.
- 15. MD 5 to Point LookoutWhy: The long run down the Southern Maryland peninsula past St. Mary's City, Maryland's first colonial capital, to the tip of the peninsula at Point Lookout State Park, between the Potomac and the bay. Loop back through Solomons Island on MD 4. Watch for: Suburban traffic at the north end, crosswinds at the point, and deer. Best season: April to June, September to November.
Summary
Maryland motorcycle roads at a glance
| Road | Region | Best season |
|---|---|---|
| Old US 40 over Town Hill | Western | May to Oct |
| Alt US 40, Cumberland to Grantsville | Western | May to Oct |
| US 219 through Garrett County | Western | Late May to mid Oct |
| MD 135, Oakland to Westernport | Western | May to Oct |
| MD 36, Georges Creek | Western | May to Oct |
| MD 51 along the Potomac | Western | Apr to Oct |
| MD 77 over Catoctin Mountain | Central | Apr to Jun, Sep to Oct |
| MD 17, Middletown Valley | Central | Apr to Oct |
| MD 34 and MD 65 at Antietam | Central | Apr to Nov |
| MD 24, Rocks State Park | Central | Apr to Oct |
| Prettyboy Reservoir roads | Central | Apr to Oct |
| MD 213 to Chestertown | Eastern Shore | Apr to Jun, Sep to Nov |
| MD 33 to Tilghman Island | Eastern Shore | May to Jun, Sep to Oct |
| MD 335 to Hoopers Island | Eastern Shore | Apr to May, Sep to Nov |
| MD 5 to Point Lookout | Southern Maryland | Apr to Jun, Sep to Nov |
Make them count
Ride Maryland's classic roads with Rippin'
The list from the app below shows the Maryland roads riders have already added. If your favorite isn't there, add it. Ride it with Rippin' recording, then open Segments and tap Create a Segment: drop a start gate and a finish gate and trace the line. A person on our team checks it, it goes live with your name on it, and every rider who rides through it after that lands on its board. More on segments and leaderboards and how roads get added.
A segment board is about who rides a road and who owns it, never a race. Rippin' doesn't reward speed on public roads, and roads like MD 77, MD 24 and the MD 135 grade are tight enough to punish it anyway.
Loops also claim turf. A Garrett County loop out MD 135 to Westernport, up MD 36 to Frostburg and home through Grantsville and US 219 closes on itself, and the land inside becomes your turf on the live map. Plan one with the loop builder and read how Turf Wars works.
Live from the app
Maryland on Rippin' right now.
4 upcoming events and 0 rider-added roads in Maryland on the map today. This list updates whenever the site is rebuilt; the app always has the latest.
- Sun Nov 1American Legion Bike Car & Truck ShowDundalk
- Sun Nov 8Lynx M.C. Annual Turkey Run 2026Joppa
- Sat Dec 12Maryland International Motorcycle Show & Swap MeetWestminster
- Sat Apr 10AMA Supercross 2027 Round 13 - BaltimoreBaltimore
No Maryland roads are in the app yet. Add the one you love from Segments and a person on our team checks it before it goes live. How roads get added.
FAQ
Questions riders ask.
What is the best motorcycle road in Maryland?
For mountain riding, old US 40 over Town Hill and the Garrett County grades on MD 135 and US 219. Closer to the cities, MD 77 over Catoctin Mountain and MD 24 through Rocks State Park. On the water, MD 33 to Tilghman Island.
What are the best motorcycle rides near Baltimore?
MD 24 through Rocks State Park, the Prettyboy and Loch Raven reservoir roads, and the farm roads of northern Baltimore and Carroll counties. For a full day, head west to Catoctin Mountain.
What are the best motorcycle rides near Frederick?
MD 77 over Catoctin Mountain, MD 17 through the Middletown Valley with a stop at Gathland State Park, and the Antietam battlefield roads around Sharpsburg.
Where is the best mountain riding in Maryland?
Garrett and Allegany counties in the far west: old US 40 over Town Hill, Alt 40 through Frostburg, MD 135, MD 36 and US 219 around Deep Creek Lake.
Are Eastern Shore roads good for motorcycles?
Yes, for relaxed riding. They're flat and mostly straight, but quiet, with water views and small towns to stop in. Watch the wind and avoid summer weekends near the beach routes.
Can I add these Maryland roads to Rippin'?
Yes. Any rider can add a road with Create a Segment. A person on the Rippin' team checks it before it goes live, and your name stays on it.
Put a Maryland classic on the map.
Download Rippin' free, ride Town Hill or Tilghman Island with it recording, and add the road. Your name stays on it.
Free on iPhone and Android. How Rippin' works
