Olivia's Overlook

Olivia's Overlook, West Stockbridge: Address, Olivia's Overlook Reviews: 4.5/5

Olivia's Overlook
4.5
Popular mentions

4.5
44 reviews
Excellent
30
Very good
10
Average
4
Poor
0
Terrible
0

Ang
11 contributions
Beautiful Overlook - but choose you trail w/care
Aug 2020
I recently went on a hike with a small group and a guide from a resort in Lenox, In our resort booklet it was listed as an easy hike. It was not. The guide led us down the charcoal trail, across and up. I'm in pretty good shape but it was a challenge going this route. When we came down from the overlook, it was an easy trail. Case in point, we could've climb up the way we came down and it would have been more enjoyable. Definitely worth the visit but pay attention to the way up you choose.
Written October 4, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC.

NYFamilyofFourRVC
Rockville Centre, NY65 contributions
Spectacular Overlook and hiking trails
Sep 2020
Must visit! Something for all levels. The Overlook is well marked and there is a beautiful view right at the parking lot if you don't have time to enjoy the hiking. The trails are well marked and can choose between short hikes or longer hikes that cross the road to visit the pond. Lots of chipmunks, stream crossings, birds. We brought picnic lunch and hiked 4-5 hours. Several stream beds were dry due to current drought but just as beautiful and fun. Several cars in parking lot but we were alone on trails most of day because of variety of trails. We chose moderate trails and there were a lot of up and down elevations so it was a great workout. Really beautiful place. Would love to visit again next time we are in the area.
Written September 27, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC.

Matthew C
6 contributions
Great Trail Run
Aug 2020
We ran the 2 mile loop, it was fantastic. Beautifully maintained trails, very well marked and easy to follow. We went early in the am and had no trouble parking. Great spot, beautiful view!
Written August 11, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC.

hornets1984
East Hartford, CT16 contributions
Beautiful
Feb 2020
Great place to hike with marked trails. Great views. Parking and trail maps are provided and convenient.
Written February 3, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC.

brendannebraska
Omaha, NE283 contributions
Worth the drive
Oct 2019 • Couples
We recently drove up to Olivia‘s Overlook while we were in the area and the view did not disappoint. The Overlook is spectacular and we were so fortunate to be in the midst of fall foliage season. If you have an opportunity to visit, we recommend it.
Written October 20, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC.

Nancy S
New York City, NY126 contributions
Outstanding Overlook
Oct 2019
Was hiking in the Berkshires and came upon Olivia's Overlook. It offers a spectacular view and great photo op!
Written October 18, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC.

W8LT3R
Howell, NJ1,901 contributions
Beautiful Backdrop for Family Photos
Aug 2019
While vacationing in the Berkshires my family and I stopped at Olivia's Overlook at the Yokun Ridge Reserve in West Stockbridge. The Overlook has a small parking lot on Richmond Mountain Road, and overlooks a beautiful lake and mountain range. There is thick stone wall between the parking lot and the view of the lake/mountains, though you can walk around this wall for an unobstructed view. Upon arrival my family immediately started taking turns shooting candid group photos of us sitting on top of the stone wall with the lake/mountain view behind us.
Besides the beautiful view Olivia's also marks the start of two hiking trails - the Charcoal Trail and the Michael H. Walsh Trail. The trail head for the Burbank Trail begins across the highway from Olivia's on Richmond Mountain Road. Our family did not do any of the trails that day.
Since the hikers park their cars in this lot and leave them until they return, when we arrived we had difficulty finding parking for our two cars. We found just one empty spot for one of our cars in the parking lot. The other car pulled into the lot and then backed out and parked beside the entrance to the Overlook just outside the parking lot. Joining several others cars that were already parked along the road.
The Overlook is along Richmond Mountain Road in West Stockbridge and is located just east of the intersection of Lenox Road and Lenox Branch Road and where Lenox Road becomes Richmond Mountain Road. Olivia's can be approached from downtown West Stockbridge on Lenox Road which becomes Lenox Branch Road ,and then you take the right turn onto Richmond Mountain Road. Olivia's Overlook will be located on your right as Richmond Mountain Road curves around. Or you can be approach Olivia's from downtown Lenox on MA 183 West to Richmond Mountain Road. From this direction Richmond Mountain Road is your typical winding mountain road with sharp turns and curves. As you are drive along Richmond Road slow down and look for the road sign for Olivia's Overlook on your left as Richmond Mountain Road curves around. (To help navigate to Olivia's I found it physical location on my GSP and set driving directions to its GSP Coordinates.)
Written September 23, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC.

DGandSAG
Sharon, MA851 contributions
Pretty Overlook and Some Good Trails in the Woods
Jul 2019 • Couples
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 some exceptions), paths were well-marked and not overly rocky or rooted.

We went in a clockwise direction -- went to the left at the first fork off the meadow by the parking area, continued quite a way's downhill, then made a steady climb up as we circled around at the end. If you go that way, hang in there -- there are two surprisingly nice vistas in the final third of the hike that overlook rolling farmland and hills nearby.

For a moderate hike mostly in the woods and with a few views, the Charcoal Trail starting at Olivia's Overlook is a good bet.
Written August 3, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC.

podrozniczka60
New Jersey13,474 contributions
Convenient starting point for hiking.
Jun 2019 • Couples
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 Old Baldhead Road etc.
The Olivia's Lookout will take just 10 minutes of your time, enough to admire the view and take pictures but you will likely enjoy the trails branching out of this spot and its vicinity.
Written July 5, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC.

vaca577779
Schenectady, NY91 contributions
Great View
Aug 2018
Nice pull-off to enjoy a pretty view of Stockbridge Bowl. A quiet spot to enjoy the peaceful Berkshire scenery.
Written January 7, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC.

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