6 Can’t‑Miss Hikes Near Woodbury And Middlebury

Woodbury and Middlebury are full of opportunities to get outside and explore the great outdoors. Whether you want a quiet forest walk or a challenging climb with rewarding views, these can’t-miss hikes in and around Woodbury and Middlebury have it all.

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. Whittemore Sanctuary

📍 CT-64, Woodbury, CT

A ~3-mile loop made up of the intersecting Purple, White and Red Trails. You'll wind up on the west shore of Lake Quassapaug, perfect for an afternoon of birdwatching and picnics by the water.

2. Trolley Bed Preserve

📍 Old Sherman Hill Road & Trolley Bed Road Intersection, Woodbury, CT

This nature preserve, located right here in Woodbury, features a picturesque pond and easy trails. Great for an afternoon out with the whole family, including dogs!

3. John A. Largay Memorial Preserve

📍 100 Long Meadow Rd, Middlebury, CT

A serene nature preserve with lush greenery and wildlife. Take the scenic 0.9-mile loop trail around Lake Elise for a quick escape into nature.

4. Wharton Brook State Park Trails

📍 675 US-5, North Haven, CT (~40 minutes)
These family-friendly trails wind along scenic brooks and waterfalls. Follow the easy to moderate routes through lush woodlands for a beautiful day in nature.

5. Prospect Mountain Preserve

📍 223 Cathole Rd, Litchfield, CT (~25 minutes)

Follow the 4.3-mile network of four trails at this beautiful nature preserve, including summits of Prospect Mountain and a loop around Granniss Pond. Excellent for spring and summer hikes.

6. Waterbury Greenway

📍 Freight St, Waterbury, CT (~15-20 minutes)

A multi-use trail following the Naugatuck River with flat terrain. It's great for casual hikers and those seeking a longer walk or bike ride.

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