Middlebury Greenway

The Middlebury Greenway is primarily a paved asphalt trail. While many rail-trails are flat, this one is surprisingly hilly with many ups and downs. The Connecticut Trail Finder lists it as 'Easy,' but some users consider it 'Moderate' due to the inclines. It is generally considered wheelchair accessible in its main paved sections. Be aware that some associated trails, like parts of the Trolley Bed Preserve Trail, are unpaved and can be quite difficult.

Parking is available at various points along the trail. A common starting point is near the eastern trailhead on CT 63. The trail also connects to several parks like Meadowview Park, Ledgewood Park, and Bristol Park, which may offer additional parking options.

Yes, the Middlebury Greenway is generally dog-friendly. Please ensure your dog is kept on a leash and that you clean up after them to maintain a pleasant experience for all trail users.

The trail offers a pleasant experience throughout the year. Spring and fall provide comfortable temperatures and scenic foliage. Summer is also popular, but be prepared for warmer weather. Winter hiking is possible, but conditions may vary, especially on unpaved sections.

No, there are no permits or entrance fees required to access and enjoy the Middlebury Greenway. It is free and open to the public.

The trail offers varied scenery, blending suburban areas with natural spots. You'll pass by natural areas near Lake Quassapaug, Lake Elise, and Fenn Pond. The route also connects to the Largay Nature Preserve and passes through several local parks.

Yes, the route also passes through sections of the Blue Trail. It also connects to the Trolley Bed Preserve Trail, which offers different terrain and difficulty levels.

The Middlebury Greenway itself is primarily an out-and-back trail. However, its connections to other local paths and parks might allow for variations or longer routes if you explore beyond the main greenway.

Yes, the trail follows the path of an historic trolley line that once connected Waterbury to Woodbury. Informational signs along the route detail this past, offering a glimpse into the area's history.

If you prefer a predominantly downhill return, consider starting your hike from the eastern trailhead on CT 63. This section features a slight uphill slope at the beginning, meaning your return journey will be easier on the way back.

While the trail itself has stone benches for rest and mile markers, you'll find amenities in the nearby suburban areas of Middlebury. The trail's proximity to Quassy Amusement Park also offers a unique destination at one end.