Bear Mountain: Connecticut's Highest Peak
Conquer Connecticut's highest peak for breathtaking tri-state views. Hike the Appalachian Trail to the summit of Bear Mountain in Salisbury.
Hike to the summit of Bear Mountain, the highest peak in Connecticut, and enjoy panoramic views of the surrounding tri-state area. The well-maintained trails, including a stretch on the Appalachian Trail, offer a challenging but rewarding experience for outdoor enthusiasts.
A brief summary to Bear Mountain
- Salisbury, Connecticut, US
Local tips
- Arrive early, especially on weekends and during peak hiking season, as the parking lot at the Undermountain Trailhead fills up quickly.
- Bring plenty of water and snacks, as the hike can be strenuous, and there are no water fountains at the trailhead.
- Wear appropriate hiking shoes and be prepared for rocky and steep sections on the trail.
- Check the weather forecast before you go and be prepared for changing conditions, especially at higher elevations.
Getting There
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Driving
To reach Bear Mountain, navigate to Salisbury, CT. From the center of town, follow Route 41 north for approximately 3 miles. Look for the Undermountain Trailhead parking area on the left. Parking is free, but the lot is small and fills up quickly, especially on weekends. Consider arriving early or carpooling. Be prepared to park along the road if the lot is full.
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Public Transport
While direct public transportation to the Bear Mountain trailhead is limited, you can take the Metro-North Railroad to the Wassaic station. From there, a taxi or ride-share service can take you to the trailhead in Salisbury, about 15 miles away. Expect to pay around $30-$40 for the taxi ride. Check train schedules and taxi availability in advance.
Discover more about Bear Mountain
Iconic landmarks you can’t miss
State Point - NY MA CT
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Copake Iron Works Historic Site
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Carl Great Barrington Memorial
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Beckley Iron Furnace State Park
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Sharon Valley Historic District
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Housatonic State Forest
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Haystack Mountain Tower
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Beartown State Forest Headquarters
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Cunningham Tower
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Henry W. Livingston House
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The Harder Mansion
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Schantz Galleries Contemporary Glass
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National Shrine of The Divine Mercy, Stockbridge, MA
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Titus Mansion Ruins
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The Berkshires
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Unmissable attractions to see
Mount Riga State Park
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Mount Everett State Reservation
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Upper Housatonic Valley National Heritage Area
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Ashley House
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Bash Bish Falls State Park
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Bartholomew's Cobble Reservation
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Taconic State Park - Copake Falls Area
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Thom Reed - UFO Monument Park
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Thom Reed - UFO Park
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Catamount Aerial Adventure Park
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Umpachene Falls Park
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Better Place Forests - Litchfield Hills
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Lower Carroll Mill Trailhead
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Sharon Historical Society & Museum
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Campbell Falls State Park
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Essential places to dine
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Blackberry River Bistro
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Caddie Shack
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McDonald's
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Mountainside Cafe
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The Bistro Box
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Great Barrington Bagel Company
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Bizalion's Fine Food
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Number Ten
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The Well Restaurant + Bar
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Bizen Gourmet Japanese Restaurant and Sushi Bar
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Baba Louie's Sourdough Pizza
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Momma Lo's Southern Style BBQ
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When Pigs Fly
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The Prairie Whale
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Markets, malls and hidden boutiques
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Stop & Shop
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100 Main
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Berkshire Great Finds & Frame Shop
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The Berkshire Galleries of Great Barrington
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The Chef's Shop At Guido's Fresh Marketplace
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Wheeler Wine Merchants
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The Edward - Wine, Cocktails, Small Plates
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Vanderbilt Lakeside Bar Room & Guesthouse
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The Lion's Den
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102 Tavern Inc
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Bucky's Tavern
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Moe's Tavern
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