Massachusetts: The Berkshires

Day 1: Hartford CT to Hadley MA
Our New England adventure begins as we land in Hartford, where airport transfers await to whisk us toward Western Massachusetts, the setting for our six-day jaunt. The drive acquaints us with the state’s character and distinctive countryside. Red barns and quiet towns hint at what’s to come. By late afternoon, we arrive at our welcoming hotel in Hadley, where we settle in and meet the group we’ll be sharing the week with. The rest of the afternoon is unhurried, a buffer between travel and the slower rhythm ahead. Some of us sit out on the patio, others find a local café for a comforting drink, while a few choose to rest, unpack, and ease into the evening.
Dinner is at Pulse Café, a former buffalo farm lovingly transformed into a fully vegan restaurant. Inside, timber beams span the high ceiling while soft light reflects off polished tables. The air carries the scent of herbs, warm bread, and vegetables roasting in the kitchen. Plates arrive generous and colorful. Think bright salads, velvety soups, seasonal mains made with local produce, and desserts that taste like love. Over the meal, we introduce ourselves and share stories that turn polite conversation into laughter. Strangers become companions, and the pace of life slows in the best possible way.
After dinner there’s time to linger for tea or step outside to watch the last of the light fade behind the hills. Back at the hotel, we fall asleep surrounded by the calm of the countryside feeling content, rested, and ready for the creative heart of New England to unfold the next morning.

Day 2: Northampton and Shelburne Falls
After breakfast at a local bagel and smoothie café, we travel west to Northampton, a town where intellect and creativity intertwine. Northampton is part of the Five Colleges area, home to Smith College, one of the country’s most respected women’s universities. This gives it a lively, youthful energy.
We wander through independent galleries, browse quirky bookshops, and pause for a drink in one of the town’s many vegan-friendly spots. Each corner invites discovery, and you quickly understand how such a small place can have such a big impact.
The journey to Shelburne Falls itself is an experience as the landscape shifts from city streets to wide fields edged with new leaves. Church steeples rise above quiet towns, and early spring flowers brighten the roadside. This is a village that feels quietly timeless. The Bridge of Flowers stretches across the Deerfield River, transformed into a walkway of color and scent. Tulips, daffodils, and early perennials sway gently in the breeze as water rushes softly below. Nearby, the glacial potholes reveal the artistry of nature, their smooth stone basins carved by time and water. Lunch is a relaxed picnic beside the river, where we can enjoy the scenery and the company of new friends.
In the afternoon we return to Hadley, our base for the next two nights. There’s time to rest, explore, or sit outside and watch the world drift by. Dinner is at a local vegan restaurant that captures the region’s warmth with wholesome food, easy laughter, and the comforting feeling that travel can still feel like home.

Meals Included
Day 1: Dinner
Day 2: Breakfast, lunch and dinner

Day 3: Cloa’s Ark Sanctuary and Brattleboro, Vermont
We ease into the day at the Wild Chestnut Café, where sunlight, good coffee, and local flavors set the tone for what’s to come. The menu celebrates local, seasonal produce with breakfast sandwiches, colorful grain bowls, roasted vegetables, and fresh desserts.
Today focuses on compassion, connection, and community. After breakfast, a short drive takes us to Cloa’s Ark Sanctuary. It’s a wonderful refuge for rescued farm animals and a haven built on love, education, and respect for all beings. The founders will lead us through open fields where cows graze, goats wander, and chickens search the grass. Each animal’s story holds both hardship and hope, reminding us how deeply connected all lives can be. Then it’s back to Pulse Café for lunch, because once just isn’t enough to sample its wonderful menu.
In the afternoon we cross into Vermont, following winding roads lined with trees and gentle hills. Our destination is Brattleboro, a town whose 1960s counterculture roots still shape its creative spirit. Artists, musicians, and idealists once came here seeking simpler lives and freer expression, forming communes that valued creativity, equality, and nature. That spirit endures in today’s art cooperatives, its fantastic food coop, and lively streets filled with independent shops and buskers. We’ll explore at our leisure before dinner.
The return to Hadley is quiet and contented. The fading light and soft conversation bring a peaceful close to a day that feels meaningful and won’t be forgotten quickly.

Day 4: Hadley to the Berkshires
After breakfast at the delicious Wild Chestnut Café, again, we say goodbye to Northampton and begin our journey west toward the Berkshires, a region where art, history, and mountain scenery blend in perfect balance. The road winds through forest and meadow, revealing white-steepled churches, cottages, and stillness. The pace is unhurried, giving us time to notice the changing light and breathe in the landscape as it unfolds.
Our first stop is Hancock Shaker Village, a beautifully preserved settlement that tells the story of a community once devoted to equality, simplicity, and craftsmanship. We walk through its round stone barn, marvel at ingenious wooden tools, and wander gardens arranged with quiet precision. Guides share insights into Shaker life, describing how design and devotion were woven into every part of daily routine. Even in silence, the place feels alive with purpose and peace.
Lunch is served nearby at a cheerful vegan diner where comfort food receives a thoughtful twist. Bowls of creamy chowder, plates of roasted seasonal vegetables, and fruit pie still warm from the oven offer a taste of simple abundance. Afterward there is time to revisit the village or browse the gift shop filled with handmade goods inspired by traditional Shaker design.
By late afternoon we arrive at The Black Swan Inn, our home for the next two nights. The inn sits on a hill beautiful serene pond. As evening settles, we gather for dinner with wood-fired pizza, local produce, and gentle conversation that drifts into laughter. The calm of the Berkshires wraps around us, and sleep comes easily in this pocket of quiet beauty.

Meals Included
Day 3: Breakfast, lunch, and dinner
Day 4: Breakfast, lunch, and dinner

Day 5: Lenox and Stockbridge
We begin the morning with a drive into town for breakfast at a cozy local café, known for its delicate crepes and friendly atmosphere. Plates arrive filled with fruit compote, warm syrup, and freshly brewed coffee, setting an easy flow for the day ahead.
After breakfast we head north to North Adams to visit MASS MoCA, the Massachusetts Museum of Contemporary Art, one of the largest and most imaginative art spaces in the country. Housed within a restored 19th-century factory complex, its red brick walls and vast halls now hold installations that defy expectation. We’ll wander through rooms alive with sound, light, and color. Towering sculptures hang from ceilings, multimedia pieces blend art and technology, and each space sparks curiosity and conversation.
Following lunch, we journey south to Stockbridge, a postcard-perfect town surrounded by soft hills and tall trees. Here we visit the Norman Rockwell Museum, home to the artist’s tender and humorous depictions of American life. Standing before his paintings feels like stepping into memory, where ordinary moments reveal quiet grace and humanity.
By late afternoon we reach Lenox, a town celebrated for its music, culture, and warm spirit. Dinner is shared at an Italian restaurant, a joyful reflection on the week so far. As the evening cools, the scent of pine drifts through the air, and the calm of the Berkshires seems to pause time itself.

Day 6: Berkshires to Connecticut
Our final morning begins quietly with a delicious breakfast and easy conversation. It’s hard to believe six days have passed so quickly. We’ve explored small towns, met kind people, and shared meals that made every stop feel special.
After check-out we travel east toward Connecticut. The road feels familiar now, passing farmhouses and open hills before giving way to the city skyline. The minivans are calm, filled with low chatter and the sound of zippers as bags are packed. Some enjoy the scenery, others exchange photos and contacts, everyone holding on to the week just gone.
When we reach Hartford, farewells come naturally. Smiles, hugs, and promises to stay in touch mark the end of the journey. Massachusetts leaves a gentle impression, a place of beauty, kindness, and steady charm that lingers long after we part.

Meals Included
Day 5: Breakfast, lunch, and dinner
Day 6: Breakfast