Olivia's Overlook
Lenox Road, Stockbridge, MA

Managed by

Berkshire Natural Resources Council

Part of

Yokun Ridge South

Information

  • Dogs allowed - Leashed
  • Family Friendly
  • Free
  • Parking
  • Scenic View
  • Water Views
Olivia's Overlook, facing southeast toward Stockbridge Bowl.

Olivia's Overlook, facing southeast toward Stockbridge Bowl.

Entrance to Olivia's Overlook (left), which is directly off Richmond Mountain Road

Entrance to Olivia's Overlook (left), which is directly off Richmond Mountain Road

Entrance to the charcoal trail located right in the parking lot.

Entrance to the charcoal trail located right in the parking lot.

Another view from Olivia's Overlook

Another view from Olivia's Overlook

  • Public Land
  • Private Land
  • Bus Route
  • Trail
  • Major Trail

About Olivia's Overlook

Olivia’s Overlook is a family-friendly roadside scenic view and trailhead managed by BNRC. The lookout offers expansive views of the Berkshires and the Stockbridge Bowl throughout the year. If looking for a relaxing experience, visitors can bring a book and picnic under the sun at the overlook parking lot. Then, for a more active adventure, visitors can explore the moderate hiking trails that leave from the lookout. The Charcoal Trail, which starts at the parking lot, will provide hikers with more scenic vistas of Western Massachusetts. Benches rest in solitude at smaller overlooks on this trail, allowing visitors to rest as they watch the clouds pass over. Across the road, the Burbank Trail will bring visitors through a whimsical pine forest. Many local wildlife species thrive in this habitat. Wildflowers, including mountain laurels, are scattered on the forest floor during springtime. Besides being an ideal spot for hikers, both the Charcoal Trail and the Burbank Trail double as mountain biking trails.

The parking lot for the overlook and trailhead is off Richmond Mountain Road before Lenox Branch Road. Although large, the lot often fills early on busy summer weekends. The BNRC property is also open to hunting at appropriate times of the year.

Berkshire Natural Resources Council

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Address

Lenox Road, Stockbridge, MA

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Accessibility Assessment

There are no accessible features at this location.

The parking lot for Olivia’s Overlook and its nearby trails is made up of smooth, compact gravel. The 3.0-mile Burbank trail loop located across the road is steep and rocky. The shorter, 1.7-mile Charcoal trail is also moderately hilly, primarily grass and dirt. The Ridge trail, a third trail extending from the parking lot, is less steep and is the flattest option out of the three trails.  

Start of the nearby Burbank Trail, located across from the parking for Olivia's Overlook

Start of the nearby Burbank Trail, located across from the parking for Olivia's Overlook

Clubs, Retail & Rentals

Looking to meet up with others for team sports or group activities? Check out our list of clubs, guides and leagues in the Berkshires on the Resources page. Our list of summer camps will help you plan an overnight or day camp adventure for your young ones.

We also link to an array of outdoor recreation retail shops for gear and rental facilities for equipment on the Gear page.

Resources Gear