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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
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
New Jersey
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  • Excellent66%
  • Very good24%
  • Average10%
  • Poor0%
  • Terrible0%
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Lenox Road, West Stockbridge, MA 01266
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Reviews (37)
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All reviews nice view parking area across the road nice hike pretty view hiking boots overlooked bowl stockbridge stop woods pond distance burbank paths
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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
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July 16, 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.