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
Pretty Overlook and Some Good Trails in the Woods

We recently hiked on the Charcoal Trail starting at Olivia's Overlook and enjoyed the workout a... read more

Reviewed August 3, 2019
DGandSAG
,
Sharon, MA
Convenient starting point for hiking.

Olivia's Lookout is not only a stop with a pretty view but also a very convenient place to park... read more

Reviewed July 5, 2019
podrozniczka60
,
New Jersey
Read all 37 reviews
All photos (16)
Full view
Traveler Overview
  • Excellent66%
  • Very good24%
  • Average10%
  • Poor0%
  • Terrible0%
Local Weather
Powered by Weather Underground
66°
44°
Sep
54°
33°
Oct
42°
26°
Nov
Contact
Lenox Road, West Stockbridge, MA 01266
Website
Improve This Listing
Reviews (37)
Filter reviews
37 results
Traveler rating
24
9
4
0
0
Traveler type
Time of year
LanguageEnglish
Traveler rating
24
9
4
0
0
Show reviews that mention
All reviews nice view parking area across the road nice hike pretty view hiking boots overlooked bowl stockbridge stop woods pond distance burbank paths
Selected filters
FilterEnglish
Updating list...
1 - 10 of 37 reviews
Reviewed August 3, 2019

We recently hiked on the Charcoal Trail starting at Olivia's Overlook and enjoyed the workout a great deal. Though we hiked on a very hot day (in the high-90s), it was reasonably comfortable (if a bit buggy) in the woods. For the most part (with...More

Date of experience: July 2019
Thank DGandSAG
Reviewed July 5, 2019

Olivia's Lookout is not only a stop with a pretty view but also a very convenient place to park your vehicle before hiking in the area. And hiking is indeed very pleasant around here. We enjoyed the Burbank Trail, Monks Pond, "John Corman homesite", walking...More

Date of experience: June 2019
Thank podrozniczka60
Reviewed January 6, 2019

Nice pull-off to enjoy a pretty view of Stockbridge Bowl. A quiet spot to enjoy the peaceful Berkshire scenery.

Date of experience: August 2018
Thank vaca577779
Reviewed November 22, 2018

This is just one of the great hiking spots near West Stockbridge. Multiple trails from this lookout point.

Date of experience: October 2018
Thank Navigate818781
Reviewed October 30, 2018 via mobile

The drive was quite pretty and longer than we thought. The overlook was very small but nice. Not sure if it was worth the drive. We didn't do any of the trails because it was getting late but could see the beautiful fall foliage over...More

Date of experience: October 2018
Thank demuslee
Reviewed October 14, 2018

It seems that most of the people who stop at Olivia’s Overlook take quick photos of the nice view, then move on. They are missing out on the opportunity to hike on two beautiful networks of trails that start at the overlook, Yokun Ridge South...More

Date of experience: October 2018
1  Thank Peter_01039
Reviewed August 29, 2018

A small parking lot for 6 or so cars. A plaque describing the place. You get a beautiful view of the valley and surrounding area. Very quiet and peaceful

Date of experience: August 2018
Thank Norma C
Reviewed October 19, 2017 via mobile

The lake looks wonderful from up here. The trees are spectacular. Wish we knew about the trails from the parking lot. Worth a stop if you’re in the area.

Date of experience: October 2017
Thank kpocampo
Reviewed July 22, 2017 via mobile

Very close to town; nice view. And walking trails too. On the same road to Tanglewood so why not stop and enjoy the view of the lake

Date of experience: July 2017
Thank brucec410
Reviewed July 2, 2017 via mobile

The view from the parking lot was spectacular. There is a good choice of trails but nothing to match the view when you arrive

Date of experience: July 2017
1  Thank KP11347
View more reviews
Nearby
Nearby HotelsSee all nearby hotels
Wheatleigh
151 reviews
1.90 miles away
Pleasant Valley Motel West Stockbridge
132 reviews
2.20 miles away
Garden Gables Inn
629 reviews
2.85 miles away
Hampton Terrace Inn
1,083 reviews
2.91 miles away
Nearby RestaurantsSee all 12 nearby restaurants
Six Depot Roastery and Cafe
180 reviews
2.00 miles away
Rouge
296 reviews
2.00 miles away
Alta Restaurant & Wine Bar
1,254 reviews
2.82 miles away
Shaker Mill Tavern
148 reviews
1.98 miles away
Nearby AttractionsSee all 16 nearby attractions
Tanglewood
1,139 reviews
1.42 miles away
Charles H. Baldwin & Sons
32 reviews
1.98 miles away
The Mount, Edith Wharton's Home
854 reviews
3.11 miles away
Questions & Answers
Ask a question
marywZ4549KB
July 16, 2017|
Answer
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.
2
Votes