A road trip into the Berkshires is a road trip back in time. A time where people didn’t have their apple watches and phones attached to their bodies at all times. The Berkshires or “the shire” as locals fondly refer to it is a place to come relax and enjoy nature. A place where there is no such thing as “wasting time” because the time you enjoy is never wasted.

From meditative hikes to canoeing the winding Housatonic river, there was never a time where one felt they were in a race. It was enough to just “be”. There are many things to do in the Berkshires. I felt like I could truly feel like I was on vacation even during a time of uncertainty in the world.

These days many may not feel safe traveling. However, around every corner, I felt safe when traveling in the Berkshires during COVID. Berkshire’s outdoor activities abound. Whether you are hiking in the Berkshires mountains or exploring beautiful fall foliage it’s the perfect escape for a long weekend.

The Berkshires covers a large portion of Western Massachusetts and I loved using Berkshires.org to plan my trip. Want more information on anything for planning your trip? They provide a great resource for planning your trip to the Berkshires.

*Disclaimer: All views and opinions are my own. This Post May Contain Sponsored Content And Or/ Affiliate Links. This Is A Way I Make An Income From My BlogI Am A Participant In The Amazon Services LLC Associates ProgramAn Affiliate Advertising Program Designed To Provide A Means For Sites To Earn Advertising Fees By Advertising And Linking To Amazon.Com.

When to visit the Berkshires

The Berkshires is beautiful year-round; however, the peak seasons is the summer season from June to August. Summer in the Berkshires offers many cultural and things to do that are unique to the “Shire”.

The beauty of the Berkshires lasts well into the fall for beautiful fall weekends exploring the foliage and changing colors from one of the many scenic drives. Also, while cold the winter in the Berkshires offers some opportunities to go skiing. So really in my opinion there is no wrong time to explore the Berkshires.

The Berkshires Outdoor Activities

There are many opportunities to explore nature around the Berkshires and a trip here would be remiss if you didn’t spend some time in the outdoors. Here is a sampling of the outdoor activities you can do to get outside in the Berkshire mountains, marshes, lakes, and rivers.

Canoe, Kayak, and Learn About Nature that has Inspired “Shire” Creatives for Centuries

My first stop when I arrived at the Berkshires, was the Housatonic River to take a journey down the snake-like windy river with Berkshire Canoe and Kayak Scenic Tours. The Housatonic River is a windy river meandering all the way to Long Island Sound.

Here see Great Blue Heron fly from their perch, and turtles getting some sun, and maybe get lucky seeing beavers playing near their dams. Summer in my opinion was the best to see the different flora and fauna in full bloom, but I can see this being even more beautiful with the fall foliage as well. Hilary, the guide and owner, has been leading trips for over 20 years and was very valuable to learn all about the Berkshires from nature to the history of the place. Whether you are a first-timer like my mom who joined me on this trip, or an experienced kayaker or canoer the 2-hour trip is enjoyable and manageable. With proper COVID precautions taken, from social distancing and masks when crossing paths I felt that it was a great experience to enjoy nature safely.

Hike and Let it All Go With Berkshire Camino

A trip to the Berkshires would not be the same without a nice hike and exploring the bucolic countryside and nature. While it is great to catch a play or eat at one of the many amazing farm-to-table restaurants, I decided I wanted to get outdoors with Berkshire Camino.

I met Mindy Miraglia at Olivia’s Overlook to learn about her tour company and get the first-hand experience of the Berkshire Camino. We began taking the Burbank Loop on the Yokun ridge, which included another overlook over West Stockbridge and the Taconic Mountain Range. Mindy started Berkshire Camino after hiking the Camino de Santiago in Spain twice! The Berkshire Camino leads guests on a journey where you walk with intention and be mindful of your surroundings. As we walked I was able to truly let go of my “rat race mindset”, and truly take in the beauty of the Berkshires. Whether you want to take a half-day or multi-day experience with Berkshire Camino, this will be a grounding experience that will have you feeling closer to nature.

She shared with me how the Berkshire Natural Resources Council is developing a “High Road” to create a system of trails to make the Berkshires 100% walkable to connect town centers in the region. I got to get a sneak peek on what the first leg will look like and it is scheduled to open in 2021 starting at Olivia’s Overlook.

Season: May through the Fall Foliage in October

Hike to the Highest Point in Massachusetts- Mount Greylock

While some love to relax and take a leisurely hike, I know some love the thrill of going to the highest peak. The highest peak in Massachusetts is Mount Greylock at 3,489 feet. Located in the western part of Adams in Berkshire County this will definitely be the most challenging hike in Massachusetts. A 3-mile strenuous hike to the top with 1100 ft elevation gain is worth it for the views!

Summer or Winter Fun At Jiminy Peak

I never knew that ski resorts such as Jiminy Peak were open in the summer! But this visit I was able to go to Jiminy Peak’s Adventure Park to explore the mountain coasters, alpine slides, and take the chair lift to the top of the mountain to have a picnic. Exploring the mountain and resort was as beautiful as ever. While I love going skiing in the winter, I definitely think it is worth a stop to explore during the summer. Jiminy Peak is right on the border of New York and close to many other Berkshire towns.

Farm to Fork Fitness Adventures (Self-Guided or Guided Tours)

The perfect mix of food and fitness has to be a cycling tour with Farm to Fork Fitness. There are self-guided cycling tours as well as guided tours throughout the North East and all involve food (my favorite thing). It is a great way to see the countryside of the Berkshires as well as get to know some local businesses in the area. The Berkshire self-guided cycle begins in Pittsfield, Massachusetts, and heads to cute towns such as Stockbridge, Massachusetts.

Bash Bish Falls

Located near Mount Washington, Massachusetts Bash Bish Falls is one of the most beautiful waterfalls in Massachusetts. Bash Bish falls are the highest in the state!

Shire Culture and Things to Do in Lenox, Stockbridge, and other Berkshire Towns

Well Read? Head to The Mount Edith Wharton’s Berkshire Estate  

Lenox, Ma

Edith Wharton is probably the most famous female author throughout time. From books such as House of Mirth and The Age of Innocence to writing the book on interior design. The Mount was Edith Wharton’s design and project that considered many architectural styles from around the world.

The beautiful accents of French, English, and Italian traditions of architecture adapted for the Berkshires American landscape permeates through the estate. I left a few hours to explore the estate’s main house, sculpted gardens, the stable, and eat on the terrace. It is worth to explore one of only 5 percent of National Historic Landmarks dedicated to women. Learn all about Edith Wharton’s individualism, drive, and unique life at The Mount. Fun Fact: Edith Wharton published 40 books in 40 years and was the first woman to win the Pulitzer Prize for The Age of Innocence.  

Visit a Maple Sugar Farm

Wandering the outskirts of Lenox, Massachusetts I found a charming family run sugar mill maple sugar farm called Mill Brook Sugarhouse. Come here to possibly get the best REAL maple syrup of your life!

Norman Rockwell Museum

Stockbridge, Ma

Explore the life, work, and art of illustration of Norman Rockwell who called the Berkshires home and derived much inspiration for his work. The museum houses the world’s largest collection of Rockwell works and is open year round!

Shop and Wander the Charming Towns of the Berkshires

Peruse the shops and unique historic architecture that can only be found in the Berkshires. My top three towns to visit in the Berkshires are Lenox, Stockbridge, and Great. Barrington. However, there are many towns that you will find along your road trip through the Berkshires that you will fall in love with.


Stockbridge, Ma

Not far from the main street in Stockbridge, is Naumkeag a former country estate and Gilded Age mansion. The vast gardens and the instagrammable pine tree-lined driveway brings you back in time.

Hancock Shaker Village

Hancock, Ma

The historic Hancock Shaker Village was active from 1790 until 1960. Now it is an open-air museum as well as on the National Register of Historic Places. The Shaker Community was one of the longest religious movements in the United States. At the height there were 300 Shakers living at Hancock Shaker Village, men and women lived separately, and they were highly regarded for their honest and industriousness.


Lenox, Ma

Tanglewood is the home of the Boston Symphony Orchestra every summer. While it was not open for business on my most recent visit. Tanglewood is the pulse of the Berkshires. Every year Tanglewood draws almost 350,000 visitors from across the world.

The School at Jacob’s Pillow

Becket, Ma

Reminiscent of the bygone days of Dirty Dancing, Jacob’s Pillow has been entertaining visitors to the Berkshires since 1931. Famous in the world of dance and still hosting classes as well as performances this is a Berkshire institution that is an experience not to miss.

Mass MoCA

North Adams, MA

Is a huge contemporary art museum with exhibits spanning almost 2 dozen buildings across an old factory in North Adams, Massachusetts. It is one of the largest centers for contemporary and performing arts in the United States and is definitely a must for art lovers in the Berkshires. Mass MoCa is open and ready to have you explore year round.

Where should I eat in the Berkshires?

The Old Heritage Tavern

12 Housatonic St Suite 201, Lenox, Massachusetts 01240

If you want casual outdoor dining the Old Heritage Tavern offers a lot of outdoor seating. Get amazing pub food with a twist, and a laidback spot to relax and fill up after a busy day exploring the outdoors.

High Lawn Farms

535 Summer Street. Lee, MA 01238

Since the 1920’s High Lawn Farms has been producing the finest Jersey Cow milk, cheese, and dairy products. This family owned and operated farm has roots in the Berkshires and today can be experienced at their farmstead creamery store on the property. Here you can get amazing ice cream, charcuterie boards, and other local products. Also, the architecture is amazing and the jersey cows are so friendly to pet.

Experience History at The Red Lion Inn

30 Main St, Stockbridge, Massachusetts 01262

The Red Lion is steeped in history and is one the oldest inns and restaurants in the United States. This historic inn has been around for two centuries and doesn’t look like it is going anywhere. I love to get a coffee and sit on the rocking chairs on the front porch. However, if you would like a fine dining experience head inside to the formal dining room.  

Head to the Lion’s Den for live music and a more laidback feel. Even locals go here so you know it is a good time!

Six Depot Roastery and Café

6 Depot Street, Town of West Stockbridge, Massachusetts 01266

Located in West Stockbridge this café is everything an art gallery, lunch spot, roastery, and a former train station. It is located in a cute village. West Stockbridge has a quaint bookstore, a country store, and art galleries to explore. Come here for locally sourced foods and a great breakfast to start off your day exploring the Berkshires.

Where should I stay in the Berkshires?

Rookwood Inn

A stay in the Berkshires would not be complete without a stay in a charming historic inn! So when I got to stay at Rookwood Inn I knew I was lucky. The summer season is usually extremely busy and staying in the center of Lenox, Massachusetts one of the most popular towns in the Berkshires is hard to do in peak season. Rookwood Inn is set on a hill in Lenox in a Victorian-era home. Every detail and room has a personal touch that brings character to the Inn.

Every morning I woke up to a great breakfast including eggs, fruit, and sometimes a cobbler. I told them to surprise me and every morning was a pleasant and filling experience. Rookwood Inn is a woman-owned business in the Berkshires. The innkeeper Amy Linder- Lesser was a gracious host and has been an active community member in the Berkshires for over 20 years. My room was everything I love pink, enchanting décor, and was very spacious. After hiking and spending the day seeing the Berkshires relaxing in my robe with some afternoon refreshments was just the cure I needed!


How can I get to the Berkshires?

It is easy to escape the city or the business of your life in the Berkshires. Conveniently located off of the Mass Turnpike and not far from NYC the Berkshires is a great trip for nature and culture lovers.

NYC to The Berkshires

From New York City to the Berkshires by car follow the parkways north to I-87 to I-90 East to Exit 2 Lee, Massachusetts. It will take you about 3 hours by car, but you will feel like you are in another world.

Boston to The Berkshires

By car it is only a 2 hour drive west on the Mass Turnpike. The ride is a straight shot. However, if you want a more scenic drive to Western Massachusetts take a ride on the Mohawk Trail (Route 2 and 2A). It will take you to picturesque spots such as the Shelburne Falls Bridge of Flowers, the Hair Pin turn in North Adams, and many other iconic spots.

Where to stay in the Berkshires?

Want to have a no-hassle time on your next trip to the Berkshires? Well here is the Ultimate Guide to the Berkshires with fun things to do. #theberkshires #theshire #massachusetts #roadtrip
Want to have a no-hassle time on your next trip to the Berkshires? Well here is the Ultimate Guide to the Berkshires with fun things to do. #theberkshires #theshire #massachusetts #roadtrip

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