or pick your starting city — the number is how many trails we list.
Pick your drive. Save time for the trail.
165 trails within 2 hr of New Haven by car. Compare the drive, the walking time and the level to choose your next outing.
Photo : Zoar Trail
Drive times are estimates (≈) from the city centre, as the crow flies. Walking time comes from the trail page when it has one; a walking filter hides trails without a duration.
Drive ≈ 47 min Walk 1 hr 15 min
Explore a working farm blended with woodland trails in rural Massachusetts: 3.2 km of easy hiking through pastoral meadows and…
Dog rules: check the trail page
See the trailDrive ≈ 1 hr 12 min
Across Litchfield County, 160.9 km of trails rated hard follow white blazes over rocky ridges, up Bear Mountain and Lion's Head… Hard trail of 160.9 km, 1829 m of climb.
Dogs allowed
See the trailCentral Massachusetts Massachusetts
Drive ≈ 45 min Walk 1 hr 30 min
Level: Moderate
Long Island New York
Drive ≈ 1 hr 1 min Walk 30 min
Level: Easy
Hudson Valley New York
Drive ≈ 1 hr 5 min Walk 2 hr 30 min
Level: Easy Dogs allowed
Long Island New York
Drive ≈ 1 hr 7 min Walk 45 min
Level: Easy Dogs allowed
Long Island New York
Drive ≈ 1 hr 8 min Walk 3 hr 15 min
Level: Easy Dogs allowed
Long Island New York
Drive ≈ 1 hr 9 min Walk 45 min
Level: Easy
Long Island New York
Drive ≈ 1 hr 10 min Walk 1 hr 15 min
Level: Easy Dogs allowed
The Berkshires Massachusetts
Drive ≈ 1 hr 16 min Walk 1 hr 15 min
Level: Easy
Long Island New York
Drive ≈ 1 hr 24 min Walk 2 hr 15 min
Level: Easy Dogs allowed
Long Island New York
Drive ≈ 1 hr 27 min Walk 1 hr 15 min
Level: Easy Dogs allowed
Hudson Valley New York
Drive ≈ 1 hr 28 min Walk 8 hr 45 min
Level: Easy Dogs allowed
Hudson Valley New York
Drive ≈ 1 hr 28 min Walk 1 hr 30 min
Level: Moderate
Hudson Valley New York
Drive ≈ 1 hr 31 min Walk 1 hr 30 min
Level: Moderate
Hudson Valley New York
Drive ≈ 1 hr 32 min Walk 2 hr 15 min
Level: Easy Dogs allowed
Hudson Valley New York
Drive ≈ 1 hr 35 min Walk 1 hr 30 min
Level: Easy Dogs allowed
Hudson Valley New York
Drive ≈ 1 hr 36 min Walk 1 hr 30 min
Level: Easy Dogs allowed
Hudson Valley New York
Drive ≈ 1 hr 39 min Walk 3 hr
Level: Moderate Dogs allowed
Hudson Valley New York
Drive ≈ 1 hr 40 min Walk 2 hr 15 min
Level: Moderate Dogs allowed
Long Island New York
Drive ≈ 1 hr 42 min Walk 45 min
Level: Easy Dogs allowed
Hudson Valley New York
Drive ≈ 1 hr 42 min Walk 5 hr 30 min
Level: Easy Dogs allowed
Hudson Valley New York
Drive ≈ 1 hr 43 min Walk 45 min
Level: Easy
Hudson Valley New York
Drive ≈ 1 hr 44 min Walk 10 hr 15 min
Level: Easy
Hudson Valley New York
Drive ≈ 1 hr 45 min Walk 1 hr 30 min
Level: Moderate Dogs allowed
Hudson Valley New York
Drive ≈ 1 hr 45 min Walk 7 hr 30 min
Level: Moderate Dogs allowed
Hudson Valley New York
Drive ≈ 1 hr 45 min Walk 2 hr 30 min
Level: Moderate
Hudson Valley New York
Drive ≈ 1 hr 46 min Walk 4 hr 30 min
Level: Hard Dogs allowed
Long Island New York
Drive ≈ 1 hr 47 min Walk 1 hr 15 min
Level: Easy
Hudson Valley New York
Drive ≈ 1 hr 47 min Walk 1 hr 30 min
Level: Moderate
Hudson Valley New York
Drive ≈ 1 hr 47 min Walk 1 hr 15 min
Level: Moderate Dogs allowed
Hudson Valley New York
Drive ≈ 1 hr 47 min Walk 2 hr 30 min
Level: Moderate
Hudson Valley New York
Drive ≈ 1 hr 49 min Walk 30 min
Level: Easy
Hudson Valley New York
Drive ≈ 1 hr 49 min Walk 1 hr 30 min
Level: Moderate Dogs allowed
Hudson Valley New York
Drive ≈ 1 hr 50 min Walk 2 hr 30 min
Level: Moderate Dogs allowed
Long Island New York
Drive ≈ 1 hr 51 min Walk 1 hr 30 min
Level: Easy Dogs allowed
Hudson Valley New York
Drive ≈ 1 hr 51 min Walk 2 hr 15 min
Level: Moderate
Northern New Jersey New Jersey
Drive ≈ 1 hr 51 min Walk 5 hr 15 min
Level: Moderate
The Berkshires Massachusetts
Drive ≈ 1 hr 53 min Walk 2 hr 30 min
Level: Moderate Dogs allowed
New York City New York
Drive ≈ 1 hr 54 min Walk 2 hr 30 min
Level: Easy
Hudson Valley New York
Drive ≈ 1 hr 56 min Walk 1 hr 30 min
Level: Easy
The Berkshires Massachusetts
Drive ≈ 1 hr 56 min Walk 2 hr 30 min
Level: Moderate Dogs allowed
Hudson Valley New York
Drive ≈ 1 hr 57 min Walk 1 hr 15 min
Level: Easy Dogs allowed
Hudson Valley New York
Drive ≈ 1 hr 58 min Walk 2 hr 30 min
Level: Easy
South Shore Massachusetts
Drive ≈ 2 hr Walk 45 min
Level: Easy
No trail matches these filters. Widen the drive or remove a filter.
Think about the way back, the breaks and the parking.
Opening hours, parking and access conditions can change with the season.
Changing weather can make some trails harder.
Match the length and the level to your group and the time you have.
Without a car, an outing takes more planning. Some destinations near New Haven may be served by public transit, but none of our trail pages lists it yet.
Check schedules and the last return trip with the transit agency before you go.
See the frequently asked questionsSpring
Spring in New Haven brings mild temperatures ranging from 50-70°F, making it ideal for exploring nearby state parks like Sleeping Giant State Park and East Rock Park.
The season offers beautiful wildflower blooms and budding trees, though trails can be muddy from snowmelt and spring rains. Pack waterproof boots and layers, as weather can be unpredictable with occasional late-season frost.
Summer
Summer hiking around New Haven features warm, humid conditions with temperatures often reaching 80-85°F and high humidity levels typical of coastal Connecticut.
Early morning or evening hikes are recommended to avoid the heat, with plenty of water essential for longer trails. The Farmington Canal Heritage Trail offers shaded sections perfect for summer walks, while coastal areas provide cooling breezes.
Fall
Fall is arguably the best season for hiking near New Haven, with comfortable temperatures in the 50-70°F range and spectacular foliage from late September through October.
The region's mixed hardwood forests create stunning displays of reds, oranges, and yellows, particularly beautiful at higher elevations like the Sleeping Giant's tower trail. Pack layers as temperatures can vary significantly between morning and afternoon.
Winter
Winter hiking around New Haven involves cold temperatures typically ranging from 20-40°F, with occasional snow and ice making trails potentially hazardous.
Microspikes or light traction devices are recommended for icy conditions, especially on rocky sections and elevated trails. Shorter daylight hours mean planning hikes to finish well before sunset, and the bare trees offer unique views of Long Island Sound from elevated vantage points.
The page lists 165 trails. The closest is Blue Trail Range (≈ 27 min drive from downtown), the farthest Seven Lakes Drive NY (≈ 2 hr). Drive times are estimated as the crow flies.
2 trails are within ≈ 30 min of driving, 9 within ≈ 1 hr, and all of them within ≈ 2 hr. These are estimates from downtown.
Among the trails on this page, the most viewed on Let's Go Play Outside are Seven Lakes Drive NY, Jaynes Hill, New York and Kings Point Park.
160 listings give a length, from 0.8 km (Wampus Pond Park) to 160.9 km (Appalachian Trail CT). The other 5 do not say.
Yes: among the trails on this page that give a level, 118 easy, 34 moderate and 3 hard. The closest easy ones: Bradley Mountain Farm, Leatherman's Cave and Wildwood State Park.
37 listings say dogs are allowed and 3 say they are not. For the other 125, the rule is not confirmed: check the trail page before you go.
Free guide: 25 hikes under 2 hours from Montreal
Drive time, distance and level for each one. The ones we go back to ourselves.
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