What are the five best things to see and do in the Berkshires?

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The Berkshires is one of New England's favorite hideaways. Located about two hours from Boston and New York City, this regional mountain range is the magic point in the middle that connects Massachusetts to the state of New York, and where everyone congregates for the same reason: complete disconnect from city life. It's in the Berkshires where you'll find endless music, theater, art and outdoor adventures. While you're here, make sure to take advantage of the following:

1. Hiking. Reconnect with nature by taking picturesque hikes through the Berkshires. October Mountains is the largest state forest in Massachusetts and includes a portion of the Appalachian Trail. The park area has a variety of different hikes for you to take on, depending on your skill level and time allotted for reconnecting with nature. For those with a little adventure in them, try to hike to Mount Greylock, the highest point in Western Massachusetts.

2. Antiquing. The Berkshires is known for many things, but those in-the-know have a very clear idea where to go when it comes to the best antique shopping in New England. Along Route 7 from Great Barrington all the way to Connecticut, antique dealers line the way selling everything from jewelry to pottery and furniture. Be sure to pick something up to take home with you.

3. Museums. Why not get cultured while you're in the Berkshires? Nothing paints the picturesque scenes of New England quite like Norman Rockwell, and you can visit the studio that houses all his famous paintings while you're here.

4. Music. The Berkshires is home to New England's favorite outdoor and indoor arts scene, including the famous Tanglewood Music Center, which is the summer home of the Boston Symphony Orchestra and you can take in concerts when you visit in July and August. Grab your blanket and picnic blanket and snag a spot on the grass outside of the open venue for $15, behind the paid seats. These tickets are a great deal and picnicking is certainly the way to go.

5. Garden tours. If there's one thing New England is known for, it's the many colors that each season brings. Fall foliage, lush summer gardens and rare spring flowers and plants bloom here throughout the year. Take a tour of the Berkshire Botanical Garden in Stockbridge, or the Ashintully Gardens in Tyringham, both small but stunning reservations that capture the beauty of the area as it changes with the seasons.

  • On May 20, 2012
    Ann Fitzpatrick-Brown answered the question: Ann Fitzpatrick-Brown

    What are the best museums in the Berkshires?

    Within a short distance of Blantyre are Edith Wharton’s The Mount, Ventfort Hall, the Clark Institute, the Norman Rockwell Museum and the Arrowhead Museum Berkshire Historical Society.
  • On May 20, 2012
    Ann Fitzpatrick-Brown answered the question: Ann Fitzpatrick-Brown

    What should I pack for a trip to the Berkshires?

    A romantic escape, any time of year, Blantyre provides outfitting for all activities on property — from snowshoes and skates to hiking boots and swim attire. Jackets and ties are required for gentleman in our dining room and whites on our tennis courts and croquet lawns. 
  • On May 20, 2012
    Ann Fitzpatrick-Brown answered the question: Ann Fitzpatrick-Brown

    What is the best way to see the Berkshires in one day?

    The best way to see the Berkshires in one day is at Blantyre. Experience a Downton Abbey of your very own at Blantyre, where guests are transported to a bygone era of gracious service, luxury and refinement.
  • On May 20, 2012
    Ann Fitzpatrick-Brown answered the question: Ann Fitzpatrick-Brown

    What’s the best time to visit the Berkshires?

    Lenox is thriving in the summer months with a bounty of outdoor activities. The fall is spectacular with colorful foliage, pumpkins and apple picking. Winter months are warmly romantic and secluded. In mid-spring as the snow melts away at the suggestion of warmer weather (a time that New Englanders refer to as “mud season”), we offer a special “Mud Package” to our guests that includes cooking classes, lessons in flower arranging and special chef menus.
  • On May 20, 2012
    Ann Fitzpatrick-Brown answered the question: Ann Fitzpatrick-Brown

    What is the Berkshires’ cultural scene like?

    A small New England village where writers and robber barons built splendid estates, Lenox and the surrounding area are known to be rich in culture and history. Tanglewood Music Center is alive with the sounds of the Boston Symphony Orchestra, as well as popular artists in concert. The Berkshire Theater Festival, Barrington Stage, Shakespeare & Company and Williamstown Theater Festival are popular among theater-goers. Jacob’s Pillow is home to an exciting dance festival. The Clark Institute, MassMOCA and the Norman Rockwell Museum round out one’s visit. 
  • On May 20, 2012
    Ann Fitzpatrick-Brown answered the question: Ann Fitzpatrick-Brown

    What are the five best free things to do in the Berkshires?

    All activities on the Blantyre property are free and exclusive to our guests. They include all sporting activities and seasonal pleasures such as winter sleigh rides and summer/fall carriage rides. In addition, here are the five best free things to do in the Berkshires:

    1. Enjoy a short walk to Edith Wharton’s The Mount and a beautiful tour of the historic house and gardens (complimentary tickets are available at our front desk).

    2. Visit Ventfort Hall, an imposing Jacobean Revival-style mansion built in 1893 for Sarah Morgan, the sister of J. P. Morgan.

    3. Take a scenic bike ride on the Ashuwillticook Trail.

    4. Stroll through the quaint village of Lenox, which dates back to the early 1700s, while window shopping and enjoying its beauty, year round.

    5. Have a restful picnic on the lawn at Tanglewood Music Center, which overlooks scenic Stockbridge Bowl. 
  • On May 20, 2012
    Ann Fitzpatrick-Brown answered the question: Ann Fitzpatrick-Brown

    Where is the best shopping in the Berkshires?

    In Blantyre’s own gift vitrine, located just off the Main Hall, guests will find a unique selection of jewelry, note cards along with special items found throughout the house. The Berkshires are well-known for charming, high-quality antique shops located throughout neighboring towns, as well as lively art galleries, craft studios and country stores. While driving on some of the area’s backroads through Connecticut and upstate New York, one will discover interesting items and wonderful country bistros, perfect for lunch.
  • On May 20, 2012
    Ann Fitzpatrick-Brown answered the question: Ann Fitzpatrick-Brown

    What are the five best things to do with kids in the Berkshires?

    At Blantyre, we welcome children over the age of 12 and encourage their participation in numerous seasonal activities, such as tennis, swimming, croquet, cross country skiing and snow shoeing — to name a few. Beyond our front gate, the best things to do with kids are:

    1. Visit the Norman Rockwell Museum in Stockbridge (20 minutes away) to enjoy original illustrated works and interactive displays of American life.

    2. Go for an invigorating hike on Monument Mountain (20 minutes away).

    3. See an exciting exhibit at MassMOCA (50 minutes away), one of the largest centers for contemporary visual installations and performing arts in the country.

    4. Spend an afternoon at Jiminy Peak Mountain Adventure Park (35 minutes away), featuring an Alpine super slide, giant swing rides, Euro bungee trampoline, rock climbing and a mountain coaster.

    5. Experience authentic Quaker daily life in Hancock Shaker Village (20 minutes away).
  • On May 20, 2012
    Ann Fitzpatrick-Brown answered the question: Ann Fitzpatrick-Brown

    What are the five best things to see and do in the Berkshires?

    The five best things to do and see in the Berkshires are:

    1. Visit a local museum. See famous works of American illustration at the Norman Rockwell Museum, or European and American Impressionist paintings at the Clark Institute. Explore contemporary art at MassMOCA or step back into the Gilded Age at Edith Wharton’s The Mount.

    2. Music concerts at the Tanglewood Music Center, the summer home of the Boston Symphony Orchestra and an ideal spot for a picnic while enjoying a concert.

    3. Shopping in antique shops and at local farmers markets and stands found while driving through the countryside.

    4. Outdoor activities. Bike or walk the Ashuwillticook Trail in Lanesboro. Kayak in Laurel Lake or ski downhill at Jiminy Peak. Go hot-air ballooning over the Berkshire Hills — depart from our back lawns. Or golf at an 18-hole course at neighboring Cranwell Resort.

    5. Enjoy a cultural experience with a play at Shakespeare & Company and the Berkshire Theater Festival, or a show at Jacob’s Pillow Dance Festival.
  • On November 12, 2011
    Forbes Travel Guide Inspector answered the question: Forbes Travel Guide Inspector

    What are the best Berkshires food experiences?

    The Berkshires area isn't necessarily known for its food. You won't vacation here because you're a foodie looking for a new experience, but instead because you're a traveler wanting to experience the historic elements of the Berkshire mountains, and at some point you're going to want to eat. Don't expect extravagantly complicated meals to occupy your dinner plate when you're here. If you're looking for something truly authentic, head straight to the diners in Lee and Lenox — our favorite is Joe's Diner, which is reminiscent of an old 1950s diner — and spin around on the bar stools while you wait for your cheeseburger and cherry coke. The Berkshires is also flanked with taverns and pubs, and anywhere you stop you'll find decent food with a New England flavor. On the menus, you’re sure to find clam chowder, chili, fish-and-chips, burgers, lobster rolls (in season) and crab cakes. We love the Barrington Brewery & Restaurant, located in Great Barrington, as it features its own brewed beers.
  • On November 12, 2011
    Forbes Travel Guide Inspector answered the question: Forbes Travel Guide Inspector

    Which five Berkshires restaurants are best for brunch?

    Before leaving the Berkshires, it's only appropriate to do a traditional brunch as only New England can do. Fill up on one of these famous brunch spots while you're here:

    1. Dakota Restaurant. The Dakota in Pittsfield was voted best restaurant in the Berkshires and best Sunday brunch. Head here for steaks, seafood, salad bars and a full kids’ menu. Sunday Brunch is served from 10 a.m. to 2 p.m., so you have plenty of time to stop in.

    2. Rumplestilzkin's at The Village Inn. Rumplestilzkin's in Pittsfield is famous for its gingerbread pancakes, a must-try when you're here for brunch, served daily during the summer and fall and on weekends in spring and winter.

    3. Joe's Diner. Who can resist greasy eggs and a side of bacon first thing in the morning? Joe's Diner in Lee is the quintessential diner in the Berkshires, offering a full breakfast menu for those needing a pick-me-up first thing in the morning.

    4. Red Lion Inn Restaurant. For a more formal brunch experience, head to the Red Lion Inn Restaurant in Stockbridge. Breakfast is served buffet-style and à la carte daily.

    5. Olde Heritage Tavern. Located in downtown Lenox, the Olde Heritage Tavern is always filled with locals and guests enjoying housemade food in a relaxed environment. Enjoy a full brunch menu on Sundays, complete with omelets, pancakes, potato hash and more.
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