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. Ragged Mountain & Spruce Mountain Trail (Georges Highland Path)

Ragged Mountain & Spruce Mountain Trail (Georges Highland Path) earns the #1 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect 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 Ragged Mountain & Spruce Mountain Trail (Georges Highland Path) trail page →Map, elevation profile, current weather, and OSM source.

#2. Rochester Commons walking / running track (0.33 mile)

Rochester Commons walking / running track (0.33 mile) earns the #2 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect gravel 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. A gravel-and-dirt tread holds up well after rain, though loose surface on descents calls for trekking poles or careful footing. 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 Rochester Commons walking / running track (0.33 mile) trail page →Map, elevation profile, current weather, and OSM source.

#3. Portland Trails Fore River Sancturary Trail (white)

Portland Trails Fore River Sancturary Trail (white) earns the #3 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect unpaved 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. A paved surface makes this one of the more accessible options on the list — good for strollers, mobility aids, and wet-weather days. 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 Portland Trails Fore River Sancturary Trail (white) trail page →Map, elevation profile, current weather, and OSM source.

#4. Cathy Schiro O'Brien Cross Country Running Trail

Cathy Schiro O'Brien Cross Country Running Trail earns the #4 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect dirt surface on a forgiving grade. Compared to similar trails in Maine, 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 Cathy Schiro O'Brien Cross Country Running Trail trail page →Map, elevation profile, current weather, and OSM source.

#5. Sentier d'accès rue des Carouges à Le Mestachibo

Sentier d'accès rue des Carouges à Le Mestachibo earns the #5 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect unpaved 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. A paved surface makes this one of the more accessible options on the list — good for strollers, mobility aids, and wet-weather days. 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 Sentier d'accès rue des Carouges à Le Mestachibo trail page →Map, elevation profile, current weather, and OSM source.

#6. Rangeley Lake Heritage Trust’s Greenvale Parcel

Rangeley Lake Heritage Trust’s Greenvale Parcel earns the #6 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect dirt 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 Rangeley Lake Heritage Trust’s Greenvale Parcel trail page →Map, elevation profile, current weather, and OSM source.

#7. Pont Roger-Pelletier (sentier Trans-Québec 30)

Pont Roger-Pelletier (sentier Trans-Québec 30) earns the #7 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect wood 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. 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 Pont Roger-Pelletier (sentier Trans-Québec 30) trail page →Map, elevation profile, current weather, and OSM source.

#8. Sentier pédestre de Saint-Bruno-de-Kamouraska

Sentier pédestre de Saint-Bruno-de-Kamouraska earns the #8 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect 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 Sentier pédestre de Saint-Bruno-de-Kamouraska trail page →Map, elevation profile, current weather, and OSM source.

#9. Thorndike Brook Trail (Georges Highland Path)

Thorndike Brook Trail (Georges Highland Path) earns the #9 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect ground surface on a forgiving grade. Compared to similar trails in Maine, 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 Thorndike Brook Trail (Georges Highland Path) trail page →Map, elevation profile, current weather, and OSM source.

#10. Ezra Smith Wildlife Conservationi Area Trail

Ezra Smith Wildlife Conservationi Area Trail earns the #10 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect dirt 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 Ezra Smith Wildlife Conservationi Area Trail trail page →Map, elevation profile, current weather, and OSM source.

Planning your Maine trip

A few pieces of context are worth keeping in mind specifically for Maine. Mid-June through early October — black flies in June, prime weather in late July and August, foliage in early October. Hypothermia in shoulder seasons, blowdown after windstorms, and rapidly changing weather on Katahdin's exposed Tablelands.

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 Maine hiking guides

If you found this useful, the rest of our Maine coverage continues below.