When hikers ask which trails in Connecticut 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 Connecticut by total mapped distance, drawing from the 4,867 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.
Connecticut is small but well-trodden — the Litchfield Hills in the northwest are the most rugged terrain, and a 52-mile stretch of the Appalachian Trail crosses the state. The Appalachian Trail and the Blue-Blazed system provide hundreds of miles of multi-day mileage despite the state's compact size. Fall foliage peaks in mid-October; summers are humid; winter brings ice-tooth conditions in shaded coves.
Our rankings here are data-driven — pulled from the 4,867 mapped entries OutsideAtlas tracks in Connecticut — 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. NET/M&M Trail (white)
At 0.10 mi, NET/M&M Trail (white) tops the list — a route built for hikers who plan in days, not hours. Expect 0.10 mi, 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 NET/M&M Trail (white) trail page →Map, elevation profile, current weather, and OSM source.#2. Maybrook Trailway - hiking - Putnam Trailway to Hopewell Junction
Maybrook Trailway - hiking - Putnam Trailway to Hopewell Junction earns the #2 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Tagged easy in OpenStreetMap. 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 Maybrook Trailway - hiking - Putnam Trailway to Hopewell Junction trail page →Map, elevation profile, current weather, and OSM source.#3. Old Canal - Latimer Neighborhood Connector Trail
Old Canal - Latimer Neighborhood Connector Trail 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 Old Canal - Latimer Neighborhood Connector Trail trail page →Map, elevation profile, current weather, and OSM source.#4. Hockanum River Linear Park - Laurel Marsh Trail
Hockanum River Linear Park - Laurel Marsh Trail earns the #4 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect wood surface on a forgiving grade. Compared to similar trails in Connecticut, this route trades difficulty for either solitude or scenery — sometimes both. 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 Hockanum River Linear Park - Laurel Marsh Trail trail page →Map, elevation profile, current weather, and OSM source.#5. Hudson Valley Greenway Trail (Pawling to Hopewell Junction)
Hudson Valley Greenway Trail (Pawling to Hopewell Junction) earns the #5 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Tagged easy in OpenStreetMap. 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 Hudson Valley Greenway Trail (Pawling to Hopewell Junction) trail page →Map, elevation profile, current weather, and OSM source.#6. Ridegfield High School Cross Country Trail
Ridegfield High School Cross Country Trail earns the #6 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect gravel 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. 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 Ridegfield High School Cross Country Trail trail page →Map, elevation profile, current weather, and OSM source.#7. Michael F. Gragnolati Conservation Trail
Michael F. Gragnolati Conservation Trail earns the #7 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect 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 Michael F. Gragnolati Conservation Trail trail page →Map, elevation profile, current weather, and OSM source.#8. Sidewalk along Charles Coleman Boulevard
Sidewalk along Charles Coleman Boulevard earns the #8 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect concrete 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 Sidewalk along Charles Coleman Boulevard trail page →Map, elevation profile, current weather, and OSM source.#9. Connecticut Water Company Trolley Trail
Connecticut Water Company Trolley Trail earns the #9 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 Connecticut, 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 Connecticut Water Company Trolley Trail trail page →Map, elevation profile, current weather, and OSM source.#10. Wilkinson Trail/Furnace Pond Loop Trail
Wilkinson Trail/Furnace Pond Loop Trail earns the #10 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect 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 Wilkinson Trail/Furnace Pond Loop Trail trail page →Map, elevation profile, current weather, and OSM source.Planning your Connecticut trip
A few pieces of context are worth keeping in mind specifically for Connecticut. Fall foliage peaks in mid-October; summers are humid; winter brings ice-tooth conditions in shaded coves. Ticks and Lyme disease are major concerns — Connecticut has some of the highest Lyme rates in the US.
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 Connecticut hiking guides
If you found this useful, the rest of our Connecticut coverage continues below.
- Steepest trails in Connecticut — Hikes with the most elevation gain in the state.
- Best beginner hikes in Connecticut — Easy, well-marked trails for first-time hikers.
- Most challenging hikes in Connecticut — Expert-rated routes for experienced hikers only.
- Best national parks in Connecticut — Federal parks and recreation areas ranked.
- Best waterfall hikes in Connecticut — Trails leading to named falls, ranked by accessibility.
- Best dog-friendly hikes in Connecticut — Where leashed dogs are explicitly welcome.
- Best family hikes in Connecticut — 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 Connecticut 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.
