Looking for the best view in the Berkshires? Olivia’s Overlook is the spot to be! Not only is Olivia’s Overlook absolutely stunning, but there are many great trails to hike around it. We’ll break down the most popular paths including the Charcoal and Burbank Trail. We’ll also provide an Olivia’s Overlook trail map to help guide you to one of the most beautiful places in the Berkshires!
Berkshires Travel Inspiration
- Planning a Visit to the Berkshires: 10 Step Fun & Easy Travel Guide
- 10 Fun Things to do in Lenox MA: Tanglewood, Nature Walks, & More
- Hiking Monument Mountain: Guide to the Best Hike in the Berkshires
- Ramblewild: Our High Flying Trip to the Aerial Adventure Park
- Bash Bish Falls: Easy Hike to the Tallest Waterfall in MA
Getting to Olivia’s Overlook in the Berkshires
Olivia’s Overlook is located in West Stockbridge on Lenox Road. After hitting the town and some of the great shops and restaurants, this is the perfect spot to take in nature. This part of the Berkshires is full of amazing hikes and walking trails, and Olivia’s Overlook Berkshires is one of our favorites!
About Olivia’s Overlook
Once you arrive at Olivia’s Overlook you’ll quickly see what all the fuss is about. The view is spectacular, as you look out over the forest and Stockbridge Bowl in the distance.
Typically you hike for miles waiting for a magical view. However, Olivia’s Overlook amazes right from the beginning! The small stone bench that lines the parking lot gives you the perfect seat to take in Olivia’s Overlook before you head out on the Charcoal or Burbank Trail.
We do have one word of caution before you start diving into the Olivia’s Overlook trail map. This is an extremely popular place year-round! If you’re visiting in the summer months make sure to go early, or plan to visit on a weekday. Also, the road can get busy so park in the main lot if possible.
Olivia’s Overlook Trail Map
Olivia’s Overlook is situated in the middle of 734 acres inside the Yokun Ridge Reserve. So after you’re done taking in the view, it’s time to head out on the 6+ miles of trail and take on an Olivia’s Overlook hike!
On the side where the lookout is you can find the entrance to the Charcoal Trail which will also take you to the Brothers Trail. Across the road, you’ll have access to the Burbank Trail that connects to Old Baldhead Road.
It’s important to note that the Charcoal and Burbank Trail distances are roundtrip while the others are one way. Also, make sure to bring any garbage with you as there are no trash cans along the paths.
Charcoal Trail: 1.6 mile loop
Brothers Trail: 0.9 miles
Burbank Trail: 3.2 mile loop
Old Baldhead Road: 1.5 miles
Our Favorite Olivia’s Overlook Hike
The Burbank Trail was an awesome Olivia’s Overlook hike, but we have to say our favorite was the Charcoal Trail! Taking about an hour roundtrip, we thought it was the perfect short hike for an afternoon in the Berkshires.
There are some ups and downs, but for the most part, it isn’t too strenuous. Also, don’t forget to stop at the vista lookout for another epic view! Want to keep hiking? You can combine the trails and spend several hours in the Yokun Ridge Reserve.
Have any questions on Olivia’s Overlook trail map, or want to share your own experience at Olivia’s Overlook in the Berkshires? Leave us a comment below!
Brigitte & Jake
Where in the world are we? Follow our daily adventures on Instagram @nothingfamiliar!
Where To Stay in The Berkshires
Ultra Luxury – Miraval Berkshires Resort & Spa – Take in some luxury in this historic Wyndhurst Mansion turned resort. Enjoy golfing, spa treatments, and views of the beautiful Berkshire countryside.
Fun Vacation – Courtyard by Marriott Lenox – Just a quick drive from downtown Lenox, this is the perfect spot to relax after a fun day of exploring. While there are plenty of historic hotels and Airbnb’s in the area, we enjoyed having the modern amenities and swimming pool at the Courtyard by Marriot.
Bed & Breakfast – Chambery Inn – This beautiful bed and breakfast is situated out in the countryside of Lee, but still close enough to walk to local restaurants and shops. You’ll also be just a few miles from attractions such a Tanglewood and Butternut Ski Resort.
Historic Hotel – Red Lion Inn – This historic hotel is a landmark in the town of Stockbridge. Stroll through town which is right at your doorstep, or simply watch the day pass you by while sipping on drinks on the front porch.
For more places to stay in the Berkshires you can explore the latest prices here!
Pin For Later ↓
USA Travel Planning
Rental Car: We use Discover Cars when traveling. Consider renting a car in one city and dropping it off in another for an epic road trip!
Tours: Check out Get Your Guide for hundreds of activities around the country. Book a tour of Fenway Park in Boston, skip the line at the Empire State Building in NYC, or go on a Sea Cave Kayak Tour in La Jolla California!
Travel Insurance: Never travel abroad without being covered! We’ve been using SafetyWing for the last few years and they are there when we need them.