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Frequently Asked Questions

The Berkshires are located in Western Massachusetts, about 140 miles north of New York City and 120 miles west of Boston. You can get to the Berkshires by train, plane, or car. 

By car, the Berkshires are about a 3 hour drive from both Boston and New York City. By train, the Berkshires are super accessible by taking Amtrak into Hudson, NY (HUD) or Pittsfield, MA (PIT). By plane, the Berkshires are conveniently located within an hour of two international airports —  Albany International Airport and Bradley International Airport. 

Time to the Berkshires:

  • From Boston: 3 hours
  • From New York: 3 hours
  • From Hartford: 1 hour
  • From Bradley International Airport: 1 hour
  • From Hudson: 1 hour
  • From Albany International Airport: 1 hour

Berkshire County is made up of 32 cities and towns and the “Berkshires” typically represent a cultural region of western Massachusetts, including the Taconic Mountains bordering New York. Geographically speaking, the following towns are some of the main towns that people visit in the Berkshires

  • Williamstown
  • Clarksburg
  • North Adams
  • Florida
  • New Ashford
  • Savoy
  • Hancock
  • Cheshire
  • Windsor
  • Dalton
  • Hinsdale
  • Peru
  • Washington
  • Middlefield
  • Adams
  • Lanesboro
  • Pittsfield
  • Richmond
  • Lenox
  • Lee
  • West Stockbridge
  • Stockbridge
  • Tyringham
  • Becket
  • Great Barrington
  • Monterey
  • Otis
  • Egremont 
  • Mt. Washington
  • Sheffield
  • New Marlborough
  • Sandisfield
  • Tolland

Some of the most popular (and fun-filled towns) in the Berkshires include Great Barrington, New Marlborough, Lenox, Lee, Stockbridge, West Stockbridge, Williamstown, and North Adams. While there are many other towns to check out, these shouldn’t be missed! 

Many towns in the Berkshires are beautiful, and great to spend time in. Each town has its special touch and we love visiting different towns for unique reasons. Lenox tends to feel “fancy” with its luxurious spas, like Miraval and Canyon Ranch, and beautiful town center. You’ll find expensive homes scattered throughout the Berkshires, like this $18M rustic retreat and this $15M modern marvel set on 300 acres. 


The absolute best way to get around the Berkshires is by car. With a car, you can explore all the best towns, attractions, restaurants, hikes, and all that make the Berkshires great! Of course, if you don’t plan on leaving a specific town you may be able to walk to things or try a ridesharing service like Uber or Lyft. 

The Berkshire Regional Transit Authority also offers bus service in and around Pittsfield and Berkshire county.

Major rental car providers, like Enterprise and Hertz, have rental locations in the Berkshires if you want to rent a car during your stay. 

Deciding where to stay during your visit to the Berkshires largely depends on the purpose of your stay, how long you’ll be there, what you want to see, and the vibe you’re going for so there’s no definite answer to the best place to stay in the Berkshires. If you’re looking to be in the center of the action and within walking distance of many attractions, consider Great Barrington, Lenox, or Stockbridge. If you want more rural, but still a short drive to the best of the Berkshires, we love New Marlborough, Stockbridge, Egremont, and Richmond. 

And if you’re looking for a cozy cottage, we recommend Oak Hill House, our lovingly restored cottage in New Marlborough. 


There are three major reasons that we fell in love with the Berkshires. The Berkshires has so many activities, especially outdoor activities, like hiking, biking, kayaking, skiing and so much more. The Berkshires are also filled with impressive, nationally recognized cultural attractions, like Tanglewood and Mass MoCA. The third reason is the absolutely delicious food sprinkled throughout the region. Many restaurants focus on locally sourced, organic and sustainable products, and you’ll find cuisines ranging from American to Vietnamese.

No matter where you decide to stay in the Berkshires, you’ll be close to all that the region has to offer. 

The Berkshires are a fantastic year-round destination. Here’s a rundown of what you can expect during each season in the region:

  • Summer: From Memorial Day to Labor Day, you’ll find the Berkshires buzzing with people looking to spend their time outside hiking, swimming in lakes, and walking around the many charming towns. Summer is the busiest and most expensive time to visit the Berkshires to be sure to plan accordingly! 
  • Spring: Late March to May is a quiet time in the Berkshires. Temperatures are on the cool side and as the snow melts, it tends to be a wet, muddy season. If you’re looking for a more affordable time to visit the region, this is a great chance to explore the area’s cultural attractions and amazing culinary destinations. 
  • Winter: Skiing, snowshoeing, tubing, and sitting by the fire are just a few of the ways to spend your days during the snowy cold months of the winter in the Berkshires. This guide is packed with what to do in the winter in the Berkshires.
  • Fall: Fall in the Berkshires is magical. As you explore the region, you’ll be greeted with crisp temperatures, stunning foliage and picturesque moments at nearly every turn. Peak fall foliage typically occurs mid October. 

We always recommend packing and wearing layers during a trip to the Berkshires. Depending on your activity, you may move from one temperature to another fairly quickly. The winter months can be very cold, so we definitely recommend bringing your winter weather gear. 

The Berkshires, with its many trendy restaurants and cultural attractions, is an extremely welcoming locale. You’ll see people wearing a range of informal and formal outfits, but you should fit right in dressing casually almost everywhere you go.  

If you’re looking to do some shopping while you’re in the area, check out the Lee Premium Outlets. Or for more seasonal gear, check out Arcadian Shop in Lenox, Barrington Outfitters in Great Barrington, or Westerlind in Great Barrington.

If you have no idea what we’re talking about, that’s okay. But if you know, you know. RHONY and RHUGT star, Dorinda Medley’s 11,000-square-foot residence has been featured on BravoTV and online. Blue Stone Manor is located in Great Barrington in the Berkshires. If you watch the show(s), you’ll notice that the cast members frequent some of our favorite places around town.

Yes! The Berkshires are a great year-round destination for families with kids of all ages. There are plenty of activities for the whole family to explore the outfoors and the area’s many cultural attractions.

Many people decide to host their wedding in the Berkshires given the area’s beautiful scenery and accessibility to major cities like New York and Boston. From farm and barn wedding venues to museums and cultural sites, the region has countless options to tie the knot and for friends and family to enjoy a lovely weekend away. The Berkshire Wedding company has resources for folks looking to plan a wedding in the region. Some popular, stunning wedding venues in the Berkshires include:

  • Gedney Farm
  • Crissey Farm
  • Berkshire Botanical Garden
  • Camp Lenox
  • Chesterwood
  • Hancock Shaker Village
  • Stonover Farm
  • The Inn at Kenmore Hall
  • The Mount
  • Wheatleigh 

If you’re attending a wedding at Gedney Farm, there are a few small inns within a 20-minute drive of the property. There are also a few hotels closer to the main towns in the Berkshires, but you’ll be about 20 minutes away from the property. Our house, Oak Hill House is 2 miles down the road from Gedney Farm. It sleeps 8 people, and provides a comfortable place to stay while in town for events.