Olivia's Overlook
Olivia's Overlook
4.5

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  • Ang
    13 contributions
    Beautiful Overlook - but choose you trail w/care
    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
  • Alden1939
    Orlando, Florida78 contributions
    Don't overlook Olivia's Overlook
    There's more to see while visiting Olivia's Overlook than the beautiful Stockbridge Bowl. There are two hiking trails, leading to an overlook site of West Stockbridge and it's surrounding area. Well worth the "at times" difficulty of the trail. You can either enter the trail going left and make a pretty rocky, somewhat steep descent, almost to the floor of the Yokun Ridge, then continue upwards at a much less ascent to the second look out point. A hidden gem, well worth the climb. If you choose to start the trail to the right, you will have to make the final ascent on the steep trail leading back to the parking lot. I say "go left" and get it out of the way! Trail is well marked, crosses a few small streams with large well placed rocks as stepping stones, and has well placed fallen trees to rest on. Moderate traffic the day I hiked but never felt crowded. Do it in the fall when the hills of West Stockbridge and Lenox are a blaze with color! When your done, take in the view from the parking lot. Well deserved after this somewhat strenuous hike.
    Written November 12, 2021
  • Rochelle F
    Randolph, New Jersey820 contributions
    Great view and nice hike
    Lovely view and quite a nice hike. We crossed the road from the parking lot and hiked the 3.2 miles hike through the forest and past the pond. Very peaceful and lovely. Lots of uphill so walking sticks are a plus. Hike name started with a "b" although forget the name now. We did this leisurely and it took us a couple of hours. Then had a picnic on the stone wall overlooking the view.
    Written June 20, 2021
These reviews are the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor checks reviews for fraud.
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NYFamilyofFourRVC
Rockville Centre, NY65 contributions
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. Tripadvisor performs checks on reviews.

Jennifer M
Philadelphia, PA96 contributions
Oct 2021
The view is beautiful!

We made a quick stop to view this hidden gem. There's a small parking lot which was convenient. Unfortunately, we were not able to do the hiking trails, but I imagine it would have been so lovely.

Definitely stop by this overlook for some gorgeous Fall foliage!
Written October 28, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

DGandSAG
Sharon, MA863 contributions
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. Tripadvisor performs checks on reviews.

Peter_01039
Western Massachusetts598 contributions
Oct 2018 • Couples
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 and Yokun Ridge North (across the road.) Those trails are quite nice, presenting opportunities for reasonably long hikes through historic properties (once owned by Andrew Carnegie) and some majestic stands of mature hemlocks. Put on some hiking boots, and take a nice hike!
Written October 14, 2018
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

hornets1984
East Hartford, CT19 contributions
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. Tripadvisor performs checks on reviews.

isletime
NC23 contributions
Jul 2016 • Family
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. It is so beautiful. Please take in this spectacular view when you are visiting the area!
Written July 30, 2016
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Joseph H
Clare, MI673 contributions
Jun 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. Plus it is FREE! :)
Written June 27, 2016
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Neil G
Boston, MA53 contributions
Feb 2016 • Couples
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.
Written February 10, 2016
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

M_Freedley
Massachusetts191 contributions
Oct 2015 • Friends
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 are walking trails along the ridge with views to the west. A small unpaved parking area gets crowded in good weather.
Written January 25, 2016
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Matthew C
6 contributions
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. Tripadvisor performs checks on reviews.

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Olivia's Overlook (West Stockbridge) - All You Need to Know BEFORE You Go

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