6 Can’t‑Miss Hikes Near Monroe

Monroe is full of opportunities to get outside and explore the great outdoors. Whether you're looking for a quick stroll or a more challenging trek, these can’t-miss hikes in and around Monroe offer something for every kind of adventurer.

Please note: Drive times are approximate and may vary based on your starting point and traffic. Be sure to check for trail closures and consider weather conditions before heading out.

1. Webb Mountain Park – Blue/Yellow/Orange Loops

📍 Webbs Hill Rd, Monroe, CT
A network of moderate loops (about 3 miles total) through 135-acre woodland with diverse flora, rock outcrops and river views; includes camping and rock climbing options.

2. Webb Mountain Discovery Zone

📍 Adjacent to Webb Mountain Park, Monroe, CT
Family-friendly and educational, this easy trail system across 170 acres features interpretive signs, scavenger-hunt paths, and a mix of forest terrain great for kids and casual hikers.

3. Paugussett Trail (Monroe Section)

📍 Access via Webb Mountain Park or Indian Well State Park, Monroe, CT
Part of the Blue-Blazed trail system, this moderate-to-strenuous through-hike connects parks and river overlooks over several miles with mixed terrain.

4. William E. Wolfe Park – Great Hollow Lake Loop

📍 285 Cutler’s Farm Rd, Monroe, CT
A roughly 4-mile easy-to-moderate trail around a 16-acre lake & wetlands, with a rustic boardwalk and swimming/fishing access; no dogs allowed.

5. Monroe Housatonic Railbed Trail

📍 Purdy Hill Rd to Pepper St, Monroe, CT
A 4.25-mile stone-dust and paved rail-trail winding through woods and farmland to the Newtown town line—flat, multi-use, and easy to follow.

6. Great Hollow Lake Short Loop

📍 Wolfe Park Area, Monroe, CT
For a quick outing, this 0.8 mi easy loop around the lake provides scenic forest and water views—perfect for families or a calm nature reset.

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