Guide to Olivia’s Overlook: Beautiful View and Fun Hiking Trails

Olivia's Overlook

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 

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! 

Olivia’s Overlook Location

Olivia's Overlook Berkshires

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 View

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 

Olivia's Overlook Trail Map

Olivia's Overlook Trail Map Photo

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. 

Packing For A Day Hike: 10 Essentials We Always Carry

Olivia's Overlook Hike

The Berkshires Olivia's Overlook

The Vista Olivia's Overlook View

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!

Safe Travels,
Brigitte & Jake

Where in the world are we? Follow our daily adventures on Instagram @nothingfamiliar

Where To Stay in The Berkshires

Ultra LuxuryMiraval 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 VacationCourtyard 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 HotelRed 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 

Olivia's Overlook Lenox MA

New England Travel Planning 

 Flights: We always find great flights using Skyscanner and Kayak. This way you can plan your trip around the cheapest and most direct routes.

 Accommodation: Compare multiple sites to get to the best deal such as and Agoda! Also, Hostelworld can be your go-to source if you’re traveling on a budget. 

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 Scenic Boat Tour in Portland Maine! 

 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.

 Packing Lists: Find all the inspiration you need with our Amazon packing lists. Including our electronics and camera gear, must-have medical items, and long flight essentials

New England Travel

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  1. rose m o
    April 27, 2022 / 7:10 pm

    There is no trash can at this parking lot please advise hikers to pack it out. We spend a lot of time removing trash from the parking lot and beyond.

    • Brigitte & Jake
      April 27, 2022 / 9:57 pm

      That’s awful! Don’t understand why people can’t pack out their own trash. We will add a note in the article thank you.

    • Brigitte & Jake
      April 1, 2022 / 8:54 am

      Thanks for sharing!

  2. Darrell
    August 7, 2021 / 4:37 pm

    The parking lot and the overlook are actually in Stockbridge. And its called Stockbridge Bowl not Berkshire Bowl.

    • Brigitte & Jake
      August 7, 2021 / 5:07 pm

      Oh true it’s right on the Lenox Stockbridge line. My whole life I just assumed it was Lenox haha! Updated thanks (-:

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