Planning a Visit to the Berkshires: 10 Step Easy Travel Guide

Have you ever thought about a vacation to the Berkshires? Western Massachusetts is home to rolling hills, endless nature, a thriving art scene, and beautiful small towns. Our Berkshires travel guide will help you plan your trip so you can jump straight to the fun! Here’s everything you need to know about planning a visit to the Berkshires.

Berkshires Travel Inspiration

• 10 Fun Things to Do in Historic Stockbridge MA on Your First Visit
• Bash Bish Falls: Easy Hike to the Tallest Waterfall in MA
• 10 Fun Things to do in Lenox MA: Tanglewood, Nature Walks, & More
• Guide to Olivia’s Overlook: Beautiful View and Fun Hiking Trails
• 9 Delicious Fall Desserts and Drinks to Enjoy in New England

Planning a Visit to the Berkshires

1. How Long is Your Berkshires Vacation?

The best part about the Berkshires is that you can have a great trip no matter what the length. Whether you only have few days to explore or a long summer holiday, it’s always a good time to visit the Berkshires!

Once you know how long you have you can start deciding what towns to explore, and which activities you’d like to do. Figuring out exactly how many days you’re in the Berkshires is the first step to planning an awesome trip. 

Berkshires Travel Guide Quick Tips

1. Plan ahead! Are you only visiting the Berkshires or is it part of a larger New England trip? 

2. If you’re coming from afar make sure to account for travel days to get you to and from the area.

3. How far do you need to book in advance? Planning for a two-night trip is going to be much different than a 2-month Berkshires vacation!

2. Where in the Berkshires to Base Yourself 

At first glance, the Berkshires may look very spread out. However, it’s also small enough to explore in just a few days! Each town is special in its own way and brings something unique to the Berkshires as a whole.

Lenox is one of our favorite places to stroll around and grab a delicious dinner outdoors. Great Barrington is a must visit with fun shops and a classic New England style. There is also Williamstown, Lee, Stockbridge, and so many more cute small towns to base yourself from.

Do your own research to see what interests you, and use that information when deciding where to stay on your Berkshires travel. 

→ 6 Best Small Towns to Explore on a Trip to The Berkshires

3. Pick a Time of Year

You’ll be happy to find out that the Berkshires is a year-round destination!

In the warmer months of spring, watch the area explode with life and tackle the great outdoors. From the quick but beautiful Monument Mountain hike to massive Mount Greylock, there are so many different walking trails to enjoy. 

Summer has always been crowned as an ideal time to visit the Berkshires. There’s plenty of great swimming at the local lakes and ponds, warm summer night concerts at Tanglewood, and general excitement surrounding the area.

Fall brings the magical colors of the leaves changing in New England and is one of the best times to be on a Berkshires vacation.

Believe it or not, even the wintertime is fun! There are several ski resorts such as Jiminy Peak, Butternut, Catamount, and Bousquet that are popular destinations for snowbirds.

The Berkshires Season Guide

• Spring: March-May
• Summer: June-August
• Fall: Sept-Nov
• Winter: Dec-Feb

4. Getting to the Berkshires 

Where are you visiting the Berkshires from? If you live in New England and are looking for a quick getaway it couldn’t be easier. The Berkshires are located two hours from Boston and just under a three-hour drive from New York City.

You can even fly into the closer airports of Albany (NY), or Bradley (CT) if you find a better deal. You will want to rent a car to maximize your time in The Berkshires. Below are the times of travel based from the starting airports to Lenox MA.

• Albany International Airport – ALB – 50 Miles – 55 Min
• Bradley International Airport – BDL – 68 Miles – 1 Hour 10 Min
• Boston Logan International Airport – BOS – 132 Miles – 2 Hours
• New York City – JFK – LGA – 150 Miles – 2 Hours 50 Min

→ 8 Top Tips For Renting a Car in Boston Massachusetts

5. Style of Visit to the Berkshires

Family Fun: The Berkshires is the perfect place for families! With an abundance of outdoor activities and local farms, it will be easy to find family-friendly fun. 

Romantic Getaway: This part of Massachusetts is for romantics. The Berkshires are filled with world-class dining and sunsets to fall in love with. 

History and Culture: New England is known for its history and the Berkshires have plenty of it. Dive into all the culture at the Hancock Shaker Village, the Clark Art Institute, and much more!

Girls Trip: Need a weekend away with the girls? Stay at a local bed and breakfast, grab some drinks, kick your feet up, and relax.

City Escape: It’s no surprise that visiting the Berkshires has become a perfect escape from the metropolis. Its bright green pastures, fresh air, and wildlife are just what you need for a break from city life.   

6. Trip to The Berkshires Cost 

Before planning any trip it’s important to take the cost into consideration. While the Berkshires are a popular destination they have also developed a reputation for being quite expensive. Ask yourself these few questions in our Berkshires travel guide prior to your visit to get an idea of what you’re willing to spend. 

• Do you need to book a flight and rental car?
• Are you visiting in the more expensive summer months?
• Does your trip fall on any holidays? 
• Are you able to visit the Berkshires in the late spring or early fall when prices are often less?
• What activities are you interested in?

7. Exploring The Berkshires 

Like we mentioned earlier in our Berkshires travel guide, you’ll need a car to get around! The towns are spaced out and there isn’t much public transportation.

If you are driving to the area that’s great as you’ll already have your own vehicle. Yet, if you’re flying in you’ll definitely want to rent a car.

Common Berkshires Routes and Distances

• Great Barrington to Stockbridge: 12 Min – 7.8 Miles
• Stockbridge to Lee: 8 Min – 4.6 Miles
• Lee to Lenox: 8 Min – 4.3 Miles
• Lenox to West Stockbrdige: 9 Min – 5.3 Miles
• West Stockbrdige to Pittsfield: 19 Min – 11.4 Miles
• Pittsfield to Adams: 23 Min – 15.3 Miles
• Adams to Williamstown: 18Min – 10.7 Miles

8. Picking the Right Accommodation

There is a range of accommodations to enjoy in the Berkshires depending on your budget. Below we break down each category to give you an idea of your options. On our last visit, we stayed at the Courtyard by Marriott which was a perfect location and base for exploring the area!

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 ideal spot to relax after a fun day of activities. 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.

Need more places to stay after reading our Berkshires travel guide? You can see the latest prices here!

9. Berkshires Vacation Activities & Fun

Once you have a place to stay on your Berkshires vacation it’s time to get to the activities! Don’t get us wrong… It’s perfectly fine to just pick up a nice book and relax on your visit. However, if you’re looking for things to do there are unlimited options.

Museums: In the mood for some art? Mass Moca and the Clark Art Institute have you covered. There is also The Mount, Naumkeag, Norman Rockwell Museum, and Hancock Shaker Village to stop into. 

Outdoor Adventures: How about some hiking? Monument Mountain, Mount Greylock, October Mountain Loop, and Kennedy Park are just a handful of the Berkshires countless hiking trails. If you’re looking for some real adventure take on the aerial adventure ropes course at Ramblewild, or go horseback riding at Berkshire HorseWorks! 

Restaurants: You’ll be happy to know that eating out in the Berkshires is an activity in itself! Just know that the best places do get busy in peak times. So if there is a restaurant you are looking forward to it’s a good idea to call ahead and make a reservation. Also, if you’re into the spirits make sure to stop in for a tasting at Berkshire Mountain Distillers.

10. Pack Your Bags and Go! 

Hopefully, by now you have a plan for your Berkshires vacation and a better understanding of this part of Massachusetts. While it’s good to have most of your trip sorted out in advance, remember where you are visiting! The Berkshires is a laid-back area that’s easy-going and all about enjoying life.

When packing it os best to consider the weather and activities you plan to do. For example, if you’ll be out in nature and hitting the hiking trails bring athletic clothing. Yet if your plan is to spend all day museum hopping then it’s obviously a much different attire. Try and plan for the weather and maybe even a little more for the unexpected. But as always… Have fun! 

In addition to our Berkshires travel guide make sure to utilize Berkshires.org as an amazing travel tool!

Check back later this summer as we continue our Berkshire blog series. We will be including more in-depth posts about each town, our favorite hiking trails, and lots more food and fun.

Have any questions about planning to visit the Berkshires? What about tips from your own visit that you want to share with others? Let us know in the comments below! 

Safe Travels, 
Brigitte & Jake

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

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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 Booking.com 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! 

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