We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Review Highlights
Great Morning Hike

This place is beautiful, with a few trails attached. We did a short loop, but I'm pretty sure you... read more

Reviewed 29 July 2016
Nathan R
Saint Paul, Minnesota, United States
Spectacular views

The view from the Overlook is spectacular and so are other views from the well kept trails. What a... read more

Reviewed 6 July 2016
via mobile
Read all 32 reviews
All photos (15)
Full view
Traveller Overview
  • Excellent70%
  • Very good21%
  • Average9%
  • Poor0%
  • Terrible0%
Travellers talk about
“parking lot”(5 reviews)
“parking area”(4 reviews)
“nice view”(3 reviews)
Local Weather
Powered by Weather Underground
Lenox Road, West Stockbridge, MA 01266
Reviews (32)
There are newer reviews for Olivia's Overlook
See the most recent reviews
Filter reviews
32 results
Traveller rating
Traveller type
Time of year
Show reviews that mention
All reviews parking lot parking area nice view walking trails hike tanglewood lake stop road trees
Updating list...
11 - 20 of 32 reviews
Reviewed 29 July 2016

This place is beautiful, with a few trails attached. We did a short loop, but I'm pretty sure you could go straight down to West Stockbridge with the ridge trail. Cool place, would hike again if in town.

Thank Nathan R
Reviewed 6 July 2016 via mobile

The view from the Overlook is spectacular and so are other views from the well kept trails. What a wonderful place.

Thank ross5100
Reviewed 5 July 2016

Beautiful view of the lake in the Berkshires. Small parking lot but people were spraying on "OFF" for their hikes and bikers were strapping on their helmets. Enjoy

Thank Wayne S
Reviewed 27 June 2016

On the advice of a local coworker, I drove up to Olivia's Overlook on my day off while in the Berkshires on business. It is a quick drive to the overlook, just past Tanglewood. It is well worth the time to enjoy the fantastic view....More

2  Thank Joseph H
Reviewed 24 May 2016

A busy out of the way spot but worth a little detour .Small parking lot great spot to hit the trail .

Thank Chuck M
Reviewed 22 May 2016 via mobile

We followed the blue rectangles which led us to Olivia's view. Beautiful. Clean and safe environment. Variety of trails. One of my favorite hikes in Berkshire county.

1  Thank Scrumple-pie
Reviewed 24 April 2016 via mobile

We've lived in the Berkshires since 1989...yet we never knew about this beautiful spot until today. We found it purely by accident while out on a Sunday afternoon ride. The view is phenomenal and the trail is well maintained. The parking lot isn't very big,...More

Thank BerkshireBaylin
Reviewed 12 March 2016

Driving up from the Red Lion Inn in the winter still made for a gorgeous drive to a stunning view. We needed the fresh air after a filling lunch. I would love to come back and hang in nature during warmer months or foliage season.

Thank capesteph511
Reviewed 10 February 2016

Right near the intersection of Lenox Rd. and Richmond Rd., Olivia's Overlook is always a stop when we travel by car or bike. THE BEST view of the Stockbridge Bowl anywhere.

Thank cycle-dad50ish
Reviewed 25 January 2016

From this high spot you will see Stockbridge Bowl (Lake Mahkeenac), Rattlesnake Hill, Beartown State Forest and Monument Mountain. An excellent place to watch the sunrise or the purple crawl of sunset from the lake up to the mountain tops. For the more adventurous there...More

1  Thank M_Freedley
View more reviews
Nearby HotelsSee all nearby hotels
141 reviews
3.05 km away
Pleasant Valley Motel West Stockbridge
127 reviews
3.55 km away
Garden Gables Inn
610 reviews
4.58 km away
Hampton Terrace Inn
1,032 reviews
4.68 km away
Nearby RestaurantsSee all 12 nearby restaurants
Six Depot Roastery and Cafe
162 reviews
3.22 km away
280 reviews
3.21 km away
Alta Restaurant & Wine Bar
1,175 reviews
4.53 km away
The Shaker Dam Coffeehouse and Stanmeyer Gallery
31 reviews
3.15 km away
Nearby AttractionsSee all 15 nearby attractions
1,049 reviews
2.29 km away
Charles H. Baldwin & Sons
29 reviews
3.19 km away
The Mount, Edith Wharton's Home
785 reviews
5.01 km away
Questions & Answers
Ask a question
Mary W
16 July 2017|
Response from VicCT |
Truely hard to find if you're trying to follow google directions. Go to the end of Lenox road all the way to the stop sign and turn right then Olivia's overlook is right there on the right.