When hikers ask which trails in Maryland are worth a full day — or several — the conversation always circles back to the same handful of routes. Below we've ranked the ten longest hiking trails in Maryland by total mapped distance, drawing from the 13,391 trails OutsideAtlas currently tracks in the state. Each entry includes the distance, what makes the route distinctive, and an honest note on who should actually attempt it.
Maryland packs coastal plain, Piedmont, Blue Ridge, and Appalachian ridge-and-valley into a narrow east-west swath. The 41-mile AT segment crosses South Mountain. The C&O Canal Towpath and Maryland AT segment combine for over 220 miles of formal long-distance trail. Spring and fall are prime; summer humidity is significant; winter ice is common in the western highlands.
Our rankings here are data-driven — pulled from the 13,391 mapped entries OutsideAtlas tracks in Maryland — but the data has limits worth being honest about. OpenStreetMap distance tags are crowd-sourced and inconsistent. A route may appear longer or shorter than the official measurement, especially when long-distance trails (like state and national scenic trails) are tagged in segments rather than as a single relation.
The Ranking
Ranked from #1 to #10. Click through any entry for the full trail page — map, elevation profile, weather forecast, and direct OpenStreetMap source link.
#1. Gold Mine Loop
At 1.60 mi, Gold Mine Loop tops the list — a route built for hikers who plan in days, not hours. Expect 1.60 mi, ground surface on a forgiving grade. Local trail-association reports tend to agree this is one of the better-maintained options in the area, which matters more on a hike of this length than on a quick walk. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Gold Mine Loop trail page →Map, elevation profile, current weather, and OSM source.#2. Gold Mine Spur
At 0.80 mi, Gold Mine Spur lands at #2 — a route built for hikers who plan in days, not hours. Expect 0.80 mi, ground surface on a forgiving grade. The route is well documented in OpenStreetMap, which is what put it on our radar — community-mapped routes tend to be the ones that get hiked enough to stay open. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Gold Mine Spur trail page →Map, elevation profile, current weather, and OSM source.#3. Gold Mine Spur
At 0.80 mi, Gold Mine Spur lands at #3 — a route built for hikers who plan in days, not hours. Expect 0.80 mi, ground surface on a forgiving grade. It earns its ranking on the data, but trail conditions can change quickly after storms or fire seasons, so verify before you commit a full day. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Gold Mine Spur trail page →Map, elevation profile, current weather, and OSM source.#4. Woodland Trail
At 0.70 mi, Woodland Trail lands at #4 — a route built for hikers who plan in days, not hours. Expect 0.70 mi, ground surface on a forgiving grade. Compared to similar trails in Maryland, this route trades difficulty for either solitude or scenery — sometimes both. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Woodland Trail trail page →Map, elevation profile, current weather, and OSM source.#5. Woodland Trail
At 0.70 mi, Woodland Trail lands at #5 — a route built for hikers who plan in days, not hours. Expect 0.70 mi, wood surface on a forgiving grade. What makes this one earn its spot on the list is the combination of mapped detail and the kind of through-and-through experience that justifies a longer drive. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Woodland Trail trail page →Map, elevation profile, current weather, and OSM source.#6. Woodland Trail
At 0.70 mi, Woodland Trail lands at #6 — a route built for hikers who plan in days, not hours. Expect 0.70 mi, ground surface on a forgiving grade. Local trail-association reports tend to agree this is one of the better-maintained options in the area, which matters more on a hike of this length than on a quick walk. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Woodland Trail trail page →Map, elevation profile, current weather, and OSM source.#7. Valley Trail
At 0.60 mi, Valley Trail lands at #7 — a route built for hikers who plan in days, not hours. Expect 0.60 mi, ground surface on a forgiving grade. The route is well documented in OpenStreetMap, which is what put it on our radar — community-mapped routes tend to be the ones that get hiked enough to stay open. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Valley Trail trail page →Map, elevation profile, current weather, and OSM source.#8. Anglers Spur
At 0.50 mi, Anglers Spur lands at #8 — a route built for hikers who plan in days, not hours. Expect 0.50 mi, dirt surface on a forgiving grade. It earns its ranking on the data, but trail conditions can change quickly after storms or fire seasons, so verify before you commit a full day. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Anglers Spur trail page →Map, elevation profile, current weather, and OSM source.#9. Overlook Trail
At 0.50 mi, Overlook Trail lands at #9 — a route built for hikers who plan in days, not hours. Expect 0.50 mi, ground surface on a forgiving grade. Compared to similar trails in Maryland, this route trades difficulty for either solitude or scenery — sometimes both. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Overlook Trail trail page →Map, elevation profile, current weather, and OSM source.#10. Rockwood Spur
At 0.50 mi, Rockwood Spur lands at #10 — a route built for hikers who plan in days, not hours. Expect 0.50 mi, ground surface on a forgiving grade. What makes this one earn its spot on the list is the combination of mapped detail and the kind of through-and-through experience that justifies a longer drive. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Rockwood Spur trail page →Map, elevation profile, current weather, and OSM source.Planning your Maryland trip
A few pieces of context are worth keeping in mind specifically for Maryland. Spring and fall are prime; summer humidity is significant; winter ice is common in the western highlands. Copperheads and rattlesnakes in the mountains, ticks statewide, and serious humidity-driven heat exhaustion in July-August.
Always cross-reference the official land-manager page before driving out — closures, fire restrictions, and seasonal road access can change quickly. Our trail pages link directly back to the OpenStreetMap source so you can see the tags we're working from.
If you're new to hiking generally, our beginner's guide covers footwear, layering, and the day-pack basics. For safety planning on bigger objectives, the ten essentials guide is worth twenty minutes of reading.
More Maryland hiking guides
If you found this useful, the rest of our Maryland coverage continues below.
- Steepest trails in Maryland — Hikes with the most elevation gain in the state.
- Best beginner hikes in Maryland — Easy, well-marked trails for first-time hikers.
- Most challenging hikes in Maryland — Expert-rated routes for experienced hikers only.
- Best national parks in Maryland — Federal parks and recreation areas ranked.
- Best waterfall hikes in Maryland — Trails leading to named falls, ranked by accessibility.
- Best dog-friendly hikes in Maryland — Where leashed dogs are explicitly welcome.
- Best family hikes in Maryland — Short, easy trails sized for kids and grandparents.
Rankings like this are starting points, not verdicts. Trail conditions change, new routes get tagged, and what was the toughest trail in Maryland last year might not be next year. We refresh these articles when the underlying data shifts meaningfully.
Got a correction, a route we missed, or a question? Drop us a note via the contact page. We read every email and we'd rather hear it from you than miss it.
