What: Housatonic Overlook at Tucker’s Ridge
Where: High Ridge Road, Orange, CT (map)
When: Year round – Best spring through fall
Admission: Free and open to the public
Trail Map: Click Here
With temperatures rising into the 60′s for the first time this year, my brother and I decided it would be a great day to head out for a hike. We went to the Housatonic Overlook at Tucker’s Ridge in Orange, which was only a few minutes drive from RT 34 down the Derby-Milford Road.
After walking only a few yards from the parking area, we found ourselves looking at a panoramic view of the Housatonic River, with the Town of Shelton facing us from directly across, Two Mile Island down below, and downtown Derby off in the distance. It was an impressive sight, and something I really enjoyed having lived in the area my whole life without realizing the overlook existed.

The most scenic point of Tucker’s Ridge is the overlook at the very beginning of the trail. According to the DEP, Bald Eagles can frequently be found flying in this are during the winter months. We didn’t see any during our hike, but I assume that was due to the fact that it was a bit late in the season.
The trail continued along the ridge and eventually became quite steep, crossing streams, wetlands and passing Mountain Laurel and rock outcroppings. A part of the trail is actually an old, abandoned dirt road known as the “Old Highway”.

While the ridge offers some great views, it’s more of an attraction for locals than anything else, and not something I’d recommend driving long distances to see.
Other things you might enjoy:Tags: All Ages, Bald Eagles, Derby, Free, Hiking Trails, Housatonic River, New Haven County, Panoramic Views












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