Escape to the Berkshires
A vacation escape for all seasons
Welcome to the Berkshires, where sophistication seamlessly blends with bucolic beauty. A gem of New England, the Berkshires have been a refuge for artists, city dwellers looking for a retreat, and anyone longing for some peace and quiet. Combining culture and the country, the Berkshire hills are home to verdant woodlands, live music and theatre, and recreational green spaces for golfing, skiing, or enjoying a day at the park.
What's Included
- Roundtrip economy class airfare to Albany (ALB)
- Automatic rental car for the duration of your trip
- Pick up and drop off ALB
- 3 nights in Stockbridge at The Red Lion Inn
- Norman Rockwell Museum Admission
Great Ways to Explore
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Visit Edith Wharton's home, The Mount.
Wander the Norman Rockwell Museum (admission is included!)
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Climb Monument Mountain.
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Tour grand estates and historic houses.
-
Spend a pleasant afternoon at the nearby Bash Bish Falls.
There are endless ways to enjoy your stay in the Berkshires. The quaint Massachusetts town of Stockbridge has a vibrant arts culture and a classic New England feel. This is the perfect place to admire the fall foliage, canoe the Housatonic River, and experience the life of 19th-century New Englanders. Known for rustic beauty, charming towns, and laid-back atmosphere, the Berkshires are everyone's cup of tea.
Please note that some recommendations in the following suggested itinerary may not be included in your package. Check What's Included above for full details on inclusions.
- Roundtrip economy class airfare to Albany (ALB)
- Automatic rental car for the duration of your trip
- Pick up and drop off ALB
- 3 nights in Stockbridge at The Red Lion Inn
- Norman Rockwell Museum Admission
-
Visit Edith Wharton's home, The Mount.
Wander the Norman Rockwell Museum (admission is included!)
-
Climb Monument Mountain.
-
Tour grand estates and historic houses.
-
Spend a pleasant afternoon at the nearby Bash Bish Falls.
There are endless ways to enjoy your stay in the Berkshires. The quaint Massachusetts town of Stockbridge has a vibrant arts culture and a classic New England feel. This is the perfect place to admire the fall foliage, canoe the Housatonic River, and experience the life of 19th-century New Englanders. Known for rustic beauty, charming towns, and laid-back atmosphere, the Berkshires are everyone's cup of tea.
Please note that some recommendations in the following suggested itinerary may not be included in your package. Check What's Included above for full details on inclusions.
Departure Airport:
Departure Month:
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Day 1. Welcome to Stockbridge!
Once you've collected your luggage, head over to the Enterprise counter to pick up your rental car. The drive from the airport in Albany to your home base in Stockbridge will take about an hour.
Once you've settled in, head out and get to know a little about the town. The adopted home of Norman Rockwell, Stockbridge has over two centuries of American history. Grab a bite at a charming, bistro-style restaurant and perhaps visit a few of the boutiques, antique stores, and other shops that line the streets of Stockbridge.
Check-in - The Red Lion Inn
The Red Lion Inn offers guests a quaint New England experience near several main attractions. The Norman Rockwell Museum, historic homes, antique shops, and ornate gardens are all nearby. With its friendly service, gourmet on-site dining options, and heated outdoor pool, The Red Lion Inn is the perfect getaway for couples, friends, and families.
Day 2. Stockbridge
Get to know Stockbridge with a visit to Naumkeag House and Gardens. Step into the Gilded Age as you explore this sprawling estate and its manicured gardens. This 44-room shingle-style home sits on 46 acres of pasture, woodlands, and gardens, overlooking Monument Mountain and the Housatonic River Valley.
In the late 1800s, post-Civil War industrialists built fabulous homes in the Berkshires to exhibit their wealth and status - which they absurdly referred to as "cottages." Over 75 of these cottages were built in villages like Stockbridge and Lenox, some of which can still be visited today.
This afternoon, visit the Norman Rockwell Museum, Ventfort Hall Mansion and Gilded Age Museum, or hit one of Stockbridge's scenic nature trails: The Mary Flynn Trail, Laura’s Tower Trail or Ice Glen Trail.
Norman Rockwell Museum Admission
The Norman Rockwell Museum is a "must-see" New England destination as the most comprehensive museum dedicated to published illustration - art that tells stories. Enjoy original art that reflects our shared humanity, history, and culture. Explore 323 Saturday Evening Post Covers by Norman Rockwell, his most iconic paintings including the defining images he created to advance the Civil Rights movement in the 1960s. The famous Four Freedoms paintings are a centerpiece at the Museum.
There’s always something new to see with changing exhibitions featuring the best in American Illustration art, to inspire your curiosity and wonder. Walk the beautiful grounds and discover sculptures by Rockwell’s son Peter, the sweeping views of the Berkshire Hills, and explore Norman’s actual studio (open May through October). The Museum Store has even more to see; shop for your favorite Rockwell prints, gifts, and books. The Runaway Café on the Museum’s scenic covered terrace offers seasonal, fresh-air dining. Lunch and snacks, ice cream, soft drinks, beer & wine are available a la carte. Picnic tables are also located on the grounds.
* Before your visit: download the free app, search “Norman Rockwell Museum” in your App Store. Use of headphones or earbuds is required in the galleries.
Day 3. Stockbridge
For a classic Berkshires experience, begin your day in Lenox. Here, you'll find iconic sights like The Mount, Edith Wharton's former stately home.
This afternoon, make your way to Pleasant Valley. With varied trails covering more than1,000 acres, the sanctuary offers hiking for every skill level and curves along the slopes of Lenox Mountain, bringing walkers through forests, meadows, and wetlands.
The Mount
Day 4. Depart Massachusetts
Today, you'll make the drive back to the Albany airport, drop off your rental car, and board your flight home.