Planning Your Berkshires Adventure: A Relaxing Getaway Guide

March 8, 2024
Flower Accent Alternative Left

Enjoy the bounty of the beautiful Berkshires in Western Massachusetts. The quaint luxury and rustic charm of this historic area offer a peaceful respite, whether for a simple weekend getaway, an artist retreat, or an extended vacation. With a bevy of hiking trails, museums, performances of theater and music, and historically and culturally important sites to explore, the Berkshires offer fun activities for solo travelers, couples, friends, and family. The Inn at Stockbridge is the perfect homebase for all the fun activities of this incredible region. 

Nature and Hiking in the Berkshires

If you crave the great outdoors, the hiking trails of the Berkshires are scenic, plentiful, and world renowned for their magnificent beauty. There are many outdoor areas for hikers, cross country skiers, mountain bikers, snowshoers, hunters, and nature lovers to explore. The Alford Springs Reserve in nearby Great Barrington features 899 acres of woodlands and trails, and Basin Pond in Lee boasts nearly 300 acres and a beaver pond. Bob’s Way and Clam River, both in Sandisfield, have multiple trail options for hikers and walkers. The Berkshire Botanical Garden is an excellent choice for flower lovers and plant aficionados. The Inn at Stockbridge sits right in the heart of all the magnificent natural resources the Berkshires have to offer. 

Skiing, Snowboarding, and Tubing in the Berkshires

Nearby ski resorts include the Bousquet Mountain Ski Area, the Berkshire East Mountain, the Butternut Ski Area and Tubing Center, Otis Ridge, and Jiminy Peak. No matter your skill level, the Berkshires has just the slope for you!

Experiences for Kids in the Berkshires

Kids can enjoy special attractions such as story time at MASS MoCA, local playgrounds, kid focused exhibits, free art making classes at the Berkshire Art Center, and child friendly nature walks and clubs at the Race Brook Lodge and Miss Audobon’s Pleasant Valley Wildlife Sanctuary. Kids will love visiting the baby cows and eating farm fresh ice cream at our neighbor High Lawn Farm. The Inn at Stockbridge has a dedicated playroom stocked with toys and games, and we even offer a suite with a children’s bedroom hidden behind a secret bookshelf door!

Activities for Kids

Historic Sites and Cultural monuments in the Berkshires

Visit the Inn at Stockbridge for an easy jaunt to Edith Wharton’s historic home The Mount, numerous monuments and historic homes, and Chesterwood, the original home of America’s foremost sculptor Daniel Chester French. Explore the fascinating history of our 280+ year old town!

Museums and Galleries in the Berkshires

The Inn at Stockbridge is a short 10-minute drive to the magnificent Norman Rockwell Museum, which features an extensive collection of Rockwell’s work in addition to revolving featured artists. Hancock Shaker Village features an intact former Shaker commune with guided tours and seasonal events for visiting history buffs.

Theater and Music in the Berkshires

The Berkshires are an epicenter of theater and music, hosting performances from the finest working actors, directors, and musicians. Visitors can enjoy the Barrington Stage Company, the Berkshire Theater Festival, and Tanglewood, the famous summer home and training academy for the Boston Symphony Orchestra and the Boston Pops. Shakespeare & Company in nearby Lenox offers guests fabulous renditions of the Bard’s greatest works. Book a cozy room at The Inn at Stockbridge for the weekend of your favorite upcoming performance!

Shopping and Dining in the Berkshires

The quaint towns and villages of the Berkshires offer an array of shopping districts to choose from. Stockbridge offers a picturesque, intimate downtown strip with cozy cafes, adorable coffee shops including The Lost Lamb and Stockbridge Coffee and Tea, and specialty stores such as Peace Love and Chocolate and the Williams & Sons Country Store. Check out nearby Great Barrington for a phenomenal downtown area if you’re interested in window shopping for antiques or craving a special cheese from Rubiner’s Cheesemongers. Lenox also offers a selection of adorable specialty shops for art, antiques, and locally made goods. 

Dining in the Berkshires

Visitors to the Inn at Stockbridge will enjoy the talented chefs and diversified cuisines of the Berkshires. Alta in Lenox offers an upscale take on Mediterranean classics. The Firefly Gastropub is also a local favorite in Lenox. Dine in the 250 year old Red Lion Inn, or travel to Mezze Bistro & Bar in Williamstown. No matter what you’re craving, you’ll find it when you stay with us here at the Inn at Stockbridge!

The Inn at Stockbridge is the perfect epicenter for your mountain getaway. Whether you’re in the mood for skiing, shopping, hiking, theater, art, or just relaxing on the porch away from it all, we have just the activity for you. Stay the night in your whirlpool suite at our bed and breakfast inside a renovated sprawling Georgian style mansion. Sit by your private fireplace as you recover from a long day of living your dream vacation. Book your room at the Inn at Stockbridge today!

Flowers Icon
About The Inn at Stockbridge

About Us


Nestled in the Berkshires, The Inn at Stockbridge offers a unique blend of historical elegance and modern comfort. Managed by innkeepers Gary and Nicole, it's a tranquil retreat known for its spacious suites, delicious breakfasts, and beautiful grounds. Perfect for relaxation and connection.

Learn More
Book Now