Road	Length	High point
Backbone Mountain / Savage River Road (MD-135) Maryland Route 135 stretches 29 miles from Oakland (US-219) in Garrett County east to McCoole (US-220) in Allegany County, crossing Backbone Mountain via a summit scenic overlook at 2,969 feet — the highest point on any Maryland state highway. The road traverses Potomac-Garrett State Forest along the ridgeline and drops steeply into the Bloomington area where it bridges the Savage River. It is part of the Mountain Maryland Scenic Byway. The Savage River Road spur off MD-135 near Bloomington adds short but exceptional forested twisties following the river downstream. The technical eastbound descent off Backbone Mountain is the most demanding section.	29 mi	—
Catoctin Mountain Highway (MD-77) Maryland Route 77 runs 20.74 miles east-west through northern Maryland, ascending South Mountain before descending Catoctin Mountain along the narrow Hunting Creek valley. The road threads between Cunningham Falls State Park to the south and the National Park Service-managed Catoctin Mountain Park to the north — the same forested ridge sheltering Camp David. The highway is designated as both the Journey Through Hallowed Ground Byway and the Old Main Streets Scenic Byway, and passes through Thurmont (junction with US-15) before extending east through Rocky Ridge to Keymar. Densely forested twisties through the park corridor are the draw; fruit stands and a covered bridge punctuate the quieter eastern farmland section.	21 mi	—
Catoctin-South Mountain Connector (MD-550) Maryland Route 550 runs 24.43 miles from Libertytown north to Fort Ritchie (Pen Mar Road), linking Frederick and Washington counties through a mix of open Monocacy Valley farmland and forested Catoctin and South Mountain terrain. The highway connects Woodsboro, Creagerstown, Thurmont, and Sabillasville, passing along the northern edge of Catoctin Mountain Park before cresting South Mountain near the Pennsylvania state line at Blue Ridge Summit. It is part of the Journey Through Hallowed Ground Byway. Fruit stands, 18th-century farmhouses, and the Victor Cullen Center dot the roadside; the northern stretch becomes genuinely mountainous as it approaches Pen Mar County Park. Pairs well with MD-77 and MD-491 for a natural Catoctin-South Mountain loop.	19 mi	—
Chesapeake Beach Bayfront Road (MD-261) Maryland Route 261 runs 12.86 miles along the western Chesapeake Bay shoreline from Parran (Calvert County) north to Friendship (Anne Arundel County), passing through the beach towns of Chesapeake Beach and North Beach and the forested Rose Haven shoreline. The road is part of the Roots and Tides Scenic Byway and parallels the bay closely as Bayside Road and Willows Road, passing the preserved Chesapeake Beach Railway Station (now a museum) and historic Holly Hill near Friendship. The ride itself is flat and shoreline-hugging rather than twisty, making it a scenic complement to the longer St. Mary's County loops or a standalone lunch-and-waterfront run out of the DC/Annapolis area.	13 mi	—
Chesapeake Country Scenic Byway (MD-213) Maryland Route 213 spans 68.25 miles up the Eastern Shore from Wye Mills (Queen Anne's County) north to the Pennsylvania state line near Fair Hill (Cecil County), threading through Centreville, Chestertown, Galena, Cecilton, and Chesapeake City. The entire route from its southern terminus to Chesapeake City is designated by the state as the Chesapeake Country Scenic Byway, with the portion north of MD-18 holding National Scenic Byway status, and the northern section carrying Atlantic to Appalachians Scenic Byway designation. The highway bridges the Chester River, Sassafras River, and the Chesapeake and Delaware Canal on a 1949 tied-arch drawbridge at Chesapeake City. Two-lane and largely rural, the road passes through some of the Eastern Shore's most intact agricultural and tidal landscape.	68 mi	—
Cunningham Falls State ParkStop The largest cascading waterfall in Maryland (78 ft) sits at the heart of Catoctin Mountain Park, right off MD-77. The William Houck Area trailhead puts riders minutes from the falls with a paved lot, picnic facilities, and a lake good for a quick dip. The park straddles the same mountain corridor that shelters Camp David, and the approach on MD-77 from Thurmont is one of the best stretches of twisties in central Maryland.	—	—
Garrett Highway — Deep Creek to Grantsville (US-219) U.S. Route 219 is the primary north-south corridor through Garrett County, running 48.40 miles from the West Virginia state line near Redhouse to the Pennsylvania border near Grantsville. Known locally as Garrett Highway, it crosses Deep Creek Lake on the Deep Creek Bridge, serves the McHenry resort area and Wisp Ski Resort, and climbs to a scenic overlook near the summit of Keyser's Ridge before intersecting I-68. The highway is designated as part of the Mountain Maryland Scenic Byway. Sweeping curves through oak-covered hills, elevation changes over 500 feet, and minimal commercial development south of McHenry characterize the southern half, while the northern section through Accident and Grantsville runs more openly through working farms and forested ridges.	49 mi	—
Harris Crab HouseStop A waterfront crab house at Kent Narrows on the Eastern Shore, just minutes off US-50/301 after crossing the Bay Bridge. Open daily 11 am–8:30 pm, it serves steamed Chesapeake blue crabs by the dozen, cream of crab soup, and crab cakes directly overlooking the narrows. The large parking lot handles bikes easily, and it's a natural anchor for any Eastern Shore day loop.	—	—
High Rock OverlookStop A drive-to-the-top viewpoint on South Mountain at roughly 1,824 ft elevation, where the Appalachian Trail crosses a graffiti-covered rock ledge with a 180-degree panorama stretching north into Pennsylvania. The road off MD-491/Pen Mar High Rock Road takes riders right to the parking lot — no hiking required. It doubles as a hang-glider launch site. Free, open year-round, and notorious for its technicolor spray-paint rock canvas.	—	—
National Road (US-40 / Alt-40 / I-68 corridor) Hancock to Keysers Ridge, ~69 mi. America's first federally funded highway; Sideling Hill cut, Casselman River Bridge, Allegheny Plateau views.	292 mi	—
Old National Pike (MD-144) Maryland Route 144 comprises multiple disconnected segments totaling roughly 57 miles that trace the old alignment of US-40 across Maryland from Cumberland to Baltimore, predating the interstate. The most scenic segment runs through the Appalachian Mountains in Allegany County (17.55 miles, Cumberland to Flintstone), paralleling I-68 through creek valleys and over Martin Mountain and Polish Mountain. The highway is part of the Historic National Road Scenic Byway and passes through Hancock, Hagerstown, Frederick, New Market, Mount Airy, and Ellicott City — home to the B&O Ellicott City Station Museum, the country's oldest surviving railroad station. The mountain sections offer the riding; the eastern piedmont and historic main streets offer the context.	18 mi	—
Sideling Hill Welcome CenterStop One of the most geologically dramatic rest stops in the eastern U.S.: I-68 slices through Sideling Hill, exposing an 850-vertical-foot syncline of 350-million-year-old Paleozoic rock in a single clean cut. The four-story exhibit center explains the geology, and a pedestrian bridge spans the highway for a rider's-eye view of the highway curving through the mountains. Open Thursday–Monday 8:30 am–4:30 pm; rest area and parking are 24/7. Located at mile marker 74, 6 miles west of Hancock.	—	—
South Mountain Pleasant Valley (MD-67) Maryland Route 67 (Rohrersville Road) runs 12.20 miles through Washington County, connecting Weverton in the south to Boonsboro in the north. The road begins at a trumpet interchange with US-340 near the Appalachian Trail's Weverton Cliffs and traverses Pleasant Valley between Elk Ridge and South Mountain, passing through Garretts Mill, Brownsville, and Gapland. Civil War terrain is ever-present: the road passes Crampton's Gap and Gathland State Park, site of the Battle of Crampton's Gap. The route is designated as part of the Antietam Campaign Scenic Byway. Tight to the western flank of South Mountain, it pairs naturally with US-340 and MD-34 for a loop connecting to Harpers Ferry.	12 mi	—
Twigg Indian MotorcycleStop Family-owned dealership in Hagerstown carrying Indian, Kawasaki, Yamaha, and Suzuki motorcycles alongside a full apparel and parts department. Open Tuesday–Friday 9 am–6 pm and Saturday 9 am–4 pm. Hagerstown sits at the crossroads of I-70, I-81, and US-40 — prime territory before or after any western Maryland mountain run.	—	—

//Rallies & events

Rally

Rally · September, ~5 days

OC Rock and Ride (Ocean City BikeFest)

Maryland

Annual five-day motorcycle rally in Ocean City, Maryland, operating as the renamed continuation of the long-running OC BikeFest. The 2026 event (September 9–13) features a Boardwalk Motorcycle Parade, vendor villages at the Inlet and Roland E. Powell Convention Center, factory demo rides, stunt shows, charity poker runs, and nightly live music. Hosted by the Greater Ocean City Chamber of Commerce.

NextSep 9–13, 2026

Official site ↗

By Switchback · Updated 2026-07-08

Best season

Late April – October

Helmet law

Required (with age/experience exceptions)

Lane splitting

Illegal (lane sharing: legal)

Signature terrain

Appalachian ridges + Chesapeake Shore

Maryland is genuinely compact — you can cover its full east-west span in a long morning — yet the state packs five distinct riding zones into that small footprint: the Appalachian ridges and river canyons of Garrett and Allegany counties, the forested Catoctin and South Mountain corridors of Frederick and Washington counties, the open Monocacy Valley farmland in between, the tidal marshes and farm roads of the Eastern Shore, and the Chesapeake bayfront south of Annapolis. None of it compares in raw technicality to the mountain roads of western North Carolina or eastern Tennessee — the curated catalog notes this plainly — but the variety per mile is hard to match in the Mid-Atlantic, and the roads are generally well-paved and lightly traveled once you step off the interstate grid.

Five Regions, One Small State

Maryland's geography is the starting point for any riding plan. The state divides cleanly into five zones, each with different road character:

Western Maryland (Garrett and Allegany counties) — the state's only genuine mountain riding. Backbone Mountain, the Savage River canyon, and the Garrett Highway corridor on US-219 are here. Elevations approach 3,000 feet; roads are steep, forested, and largely free of traffic.
Catoctin and South Mountain (Frederick and Washington counties) — a string of parallel north-south ridges with well-maintained two-lane roads, Civil War history at nearly every gap, and the Catoctin Mountain Park corridor threading between them. MD-77, MD-550, MD-491, and MD-67 anchor this zone.
Monocacy Valley and Piedmont — the rolling farmland connecting the mountains to the east. Lower drama, but useful connector mileage and the Historic National Road (US-40/MD-144).
Eastern Shore — flat, wide-sky riding through intact tidal and agricultural landscape. MD-213 runs 68 miles up the Shore; MD-261 hugs the western bay. Pace is relaxed; the payoff is seafood and open water.
Southern Maryland — longer, gentler loops down the western Chesapeake Shore, suited to riders who want mileage over technicality.

Choosing Your Route

If you want the most technical pavement in the state, head to the Savage River spur off MD-135 near Bloomington — tight river-canyon corners, steep grades, minimal traffic. Pair it with the Backbone Mountain summit on MD-135 for the state's highest paved point. Manage expectations going in: this is the state's best technical riding, not a regional benchmark.

For a full day with variety, the Catoctin-South Mountain loop (MD-77 / MD-550 / MD-491 / MD-75, roughly 60–70 miles from Libertytown) is the most consistently rewarding circuit in central Maryland. Forested twisties through Catoctin Mountain Park give way to apple-orchard farmland and back again.

Eastern Shore riders should plan around tides and flooding on low-elevation county roads, especially after heavy rain. MD-261 along the Chesapeake can flood at road level.

Practical Hazards

Deer are the constant risk statewide — the Catoctin corridor and Eastern Shore farm roads are both high-density zones, especially at dawn and dusk. On mountain roads after winter or a hard rain, sand and gravel collect in apexes and at the bottom of steep descents. The technical eastbound drop off Backbone Mountain on MD-135 deserves particular attention: the grade is significant and the surface can hold debris. Check the Maryland CHART road conditions system (chart.maryland.gov) before western Maryland rides in early spring.

// ShareFacebook Reddit X

// Frequently asked

As of October 1, 2025, Maryland created a limited exception: riders who are at least 21 years old and have held a motorcycle license for two or more years, or have completed an MVA-approved safety course, may ride without a helmet. All other riders and passengers must wear a DOT-approved helmet with the chin strap fastened. Eye protection is also required unless the motorcycle has a windscreen.

No. Both lane splitting and lane filtering are prohibited under Maryland Transportation Code §21-1303. Motorcyclists must occupy a full lane, just like other vehicles. Two motorcycles may, however, share a single lane riding side-by-side — that is legal.

Late spring through early fall — roughly May through September — is the practical window for Garrett County and Allegany County roads like Backbone Mountain (MD-135), Savage River Road, and US-219. Garrett County is one of the snowiest regions east of the Rockies, and its roads, including MD-135 and US-219, are snow emergency routes in winter. Spring melt can leave sand and gravel on mountain roads into April.

Honestly, no. The curated notes for this guide state plainly that Savage River Road — the most technical pavement in the state — is 'milder than the Dragon.' Maryland lacks a Deals Gap equivalent. What it does have is consistent variety: forested mountain twisties in the Catoctins and on South Mountain, river-canyon roads in Garrett County, and long, unhurried byway mileage on the Eastern Shore.

Sand and gravel washed across mountain roads after spring rain or winter clearing is the top hazard on western routes. Deer are abundant statewide, especially at dawn and dusk — the Catoctin and South Mountain corridors and the Eastern Shore farm roads are high-risk zones. Low-lying Eastern Shore routes like MD-261 can flood after heavy rain. The Savage River Road spur is a narrow canyon road; expect oncoming vehicles in the center of the lane on blind corners.

Oakland and McHenry in Garrett County put you within a few miles of US-219, MD-135, and the Savage River area. Hagerstown sits at the crossroads of I-70, I-81, and US-40 — Twigg Indian Motorcycle is there — and makes a practical anchor for South Mountain, the National Road corridor, and the Catoctin loop. Thurmont, on US-15, is the natural starting point for MD-77 and MD-550.

//Sources & references

Maryland SB 397 — Motorcycle Helmet Law Exception (effective October 1, 2025) ↗Maryland Motorcycle Helmet Law 2025 — Law Tigers ↗Maryland Motorcycle Laws: Lane Splitting — Hardball Law ↗Maryland Motorcycle Rides — REVER (Riding Season Overview) ↗Garrett County Snow Emergency Plan — Deep Creek Times ↗