Hit the Trails for the Best Hikes in the Berkshires

Now considered one of the cultural hubs of the world, the Berkshires’ background is rooted in nature. Before the artists, authors and poets, Gilded Age estates, The Boston Symphony at Tanglewood, Norman Rockwell, and all the world-class attractions that have evolved since, there existed natural beauty. Leonard Bernstein often said he could tell he was “home” by the smell of the Berkshires… earthy, lush and fertile. Summer is an eternal Spring.
With many of our cultural attractions closed or limited, this summer has become a once-in-a-lifetime opportunity to experience the beauty of the Berkshires without the crowds. What better way to enjoy nature than with a trek down some of the best hikes in the Berkshires. Meet one of our favorite guests, and check out her top 3 favorites places to hike, out of the hundreds of options near our Lenox bed and breakfast.
Hiking Trails Berkshires by Wanda Hopkins
Wanda has been visiting Lenox since the mid-80s and has stayed at Hampton Terrace Inn over 60 nights in the past twelve years. She goes hiking almost every day while in the area, before enjoying dinner and cultural attractions in the evenings.

“I appreciate Lenox and the warmth of the village. In addition I enjoy the Hampton Terrace Inn because of the history Stan and Susan have maintained. The delicious breakfast and interesting folks who are there in the Inn keep me returning. Waking up to sunshine and birds and cool air in the fall is always memorable. There is some southern hospitality detected as well. Come on back y’all.”

 – Wanda S. Hopkins


Let’s Play, “Where’s Wanda?”

There’s nobody around who knows about the best hikes near Lenox like Wanda. Let’s see if you can figure out which nature area she’s enjoying with a few clues… can you guess all three?

1. This First Nature Area Will Leave You Feeling Presidential, Even Though it’s Not Named After One


Kennedy Park Berkshire Trail

  • It has 500 acres, with 15 miles of trails to explore
  • It’s just 1.4 miles north of Hampton Terrace Inn
  • It is owned and maintained by the town of Lenox
  • It offers hikes from easy to difficult, and is loved by mountain bikers
  • You can walk along well maintained historic trails, which used to serve as buggy roads!
  • It was the site of the Aspinwall Hotel in the early 1900s, which burned down years ago
  • It’s named after a beloved Berkshire conservationist
  • Even though there is plenty of free parking, some hikers and bikers like to start their adventure at the Arcadian Shop, where you can pick up a map of trails (or download one here from the city). Trust us, you’ll need one!

Wanda is in Kennedy Park

Wanda’s Favorite Part: She loves that she gets to march through history at Kennedy Park, and be exposed to glades, rock outcroppings and to boundaries that once existed in the early 1800s.



2. This Second Lenox Hiking Area Has a Name as Nice at its Views


Pleasant Valley Nature Sanctuary is a Fantastic Berkshires Trail

  • It has over 1,000 acres, with 7 miles of trails to trek
  • It’s just under 3 miles north of Hampton Terrace Inn
  • It offers a variety of simple to challenging hikes, for everyone to enjoy
  • An accessible boardwalk leads you to Pike’s Pond, for superior birdwatching
  • A more strenuous hike heads up Lenox Mountain, for spectacular views of the Berkshires

Wanda is at Pleasant Valley Nature Sanctuary

Wanda’s Favorite Part: She loves walking through the towering hemlock to gaze at the streams and small waterfalls, and spot the beavers in the pond at Pleasant Valley.


3. The Third, and Tallest, Spot for Hiking in the Berkshires will Color Your World


Mount Greylock State Reservation - Hiking Trails in the Berkshires

  • It has 70 miles of trails on over 12,000 acres. Talk about a hiker’s paradise!
  • At over 3,000 feet high, it’s the state’s tallest peak
  • It’s about 24 miles north of the Inn, so you can enjoy a scenic drive
  • This area is best for more serious hikers
  • You can see for almost 90 miles from the top on a clear day
  • The top of the mountain is home to Veterans War Memorial Tower
  • Chosen by J.K. Rowling as the setting for the magical Ilvermorny School of Witchcraft and Wizardry – her American counterpart to the famed Hogwarts in Harry Potter

Wanda is at Mount Greylock State Reservation

Wanda’s Favorite Part: Although there are several favorite trails at Mount Greylock to hike, Wanda particularly enjoys Jones Nose. This trail climbs through a meadow into a steep uphill rocky trail. It can be arduous for those not prepared for this sort of hike. Good hiking boots, a walking stick, and notifying someone of your plans are highly recommended.

 Luxury Lodging Near Berkshire Hiking Trails

Let Us Be Your Luxury Base Camp

After an invigorating day of hiking, Wanda loves to come home to the Hampton Terrace Inn for rest and relaxation. We have plenty of outdoor sitting areas to enjoy, a heated pool to lounge in, and a unique BYOB bar at which to gather. Our exceptional King Suite Cottages provide private entries and porches, making them the perfect place to safely unwind after a day spent exploring the natural splendor in the Berkshires. Only a five minute walk from the historic center of Lenox, our ideal location makes us a perfect base camp to enjoy the best hiking trails in the Berkshires and warm southern hospitality. We’re always happy to guide you to your ideal hike near our quaint historic inn – or maybe you’ll get lucky and run into Wanda while you’re here!