Unearth The Voyage
Explore the hidden culinary gems of the Massachusetts Berkshires with these 13 charming pie shops, each offering unique flavors and local charm. From European-inspired bakeries to cozy cottage settings, these spots are a must-visit for pie lovers. Discover the stories and craftsmanship behind every delicious slice.
1. Taft Farms Market – Great Barrington
Taft Farms is a slice of Berkshire life. Family-run since the 1960s, it’s famous for its farm-grown produce and flaky, fruit-filled pies. Each pie is baked daily, using apples, rhubarb, berries, or pumpkins from local farms.
Seasonal favorites like strawberry-rhubarb and maple pecan sell out quickly. In fall, the aroma of pies mingles with cider and hayrides, creating a quintessential New England experience. Locals praise the buttery crusts and just-right sweetness.
Whether you stop for lunch or load up a pie to go, Taft Farms delivers pure comfort in every slice. Its laid-back, country feel is irresistible to both locals and visitors alike.
2. Cakewalk Bakery & Café – Lee
Hidden on a quiet side street, Cakewalk Bakery & Café is a delightful discovery. Known for scratch-made desserts, this bright shop makes pies that balance homemade warmth with bakery finesse.
Apple crumb, coconut cream, and mixed berry pies are staples, and in summer, local peach pies steal the show. Everything is baked fresh daily, using ingredients from nearby farms.
The café’s small seating area invites you to linger over coffee and a slice, surrounded by the smell of butter and cinnamon. Simple, charming, and unmistakably Berkshires, Lee locals swear by their pies for family gatherings.
3. Haven Café & Bakery – Lenox
Haven Café in Lenox is loved for brunch and baked goods, but their pies deserve equal attention. Baked fresh each morning, they often feature seasonal ingredients – apple in fall, blueberry in summer.
Each pie has a golden, flaky crust with farm-fresh fillings. The café’s rustic ambiance and friendly staff make it a welcoming stop after exploring downtown Lenox.
Many locals grab a slice early before they sell out. Paired with a cappuccino or Haven’s signature quiches, these pies showcase the Berkshires’ love of handcrafted, down-to-earth food done right.
4. Berkshire Mountain Bakery – Housatonic
Berkshire Mountain Bakery is renowned for its European-style breads, but the pies are a local secret. Using natural sourdough starter, they craft crusts with unforgettable depth.
Inside, seasonal fruit fillings like apple, peach, blueberry, and cherry shine with minimal sugar. The bakery’s rustic space in Housatonic fills with the comforting aroma of fresh dough.
Locals often say it’s the place where “bread people become pie people.” Perfect for a treat after hiking or a road trip, this bakery’s pies prove that simplicity and quality never go out of style.
5. The Lost Lamb – Stockbridge
The Lost Lamb is a tiny, elegant bakery in Stockbridge, where each pie feels like edible art. Pastry chef Claire Raposo, trained in Paris, brings a French touch to Berkshire traditions.
Her pies – apple tarte fine, lemon curd tart, and chocolate ganache – combine delicate technique with bold flavors. The shop feels like a secret pâtisserie, with marble counters and golden light.
Locals stop for morning coffee and a slice before strolling Main Street. Everything here is baked in small batches, so once they’re gone, they’re gone. The Lost Lamb embodies the rare mix of European precision and small-town warmth.
6. Bailey’s Bakery – North Adams
In North Adams, Bailey’s Bakery is a true local gem. This family-run shop has been turning out pies, donuts, and pastries for years, earning a devoted following.
Their pies are traditional – think apple, pumpkin, and blueberry – but executed with care and expertise. Bailey’s crusts are golden and buttery, while the fillings are packed with real fruit.
The décor is simple, the atmosphere unpretentious, and the service friendly. Whether you’re fueling up before a museum visit or grabbing dessert for the family, Bailey’s offers that “tastes-like-home” comfort that defines Berkshire baking at its best.
7. The Shire Cottage Bakery – Adams
Tucked into Adams, The Shire Cottage Bakery feels like stepping into a storybook. The scent of butter and sugar greets you before you even open the door.
Everything here is baked by hand – no shortcuts, no preservatives. Their pies are the highlight: apple-cranberry in fall, maple custard in winter.
Locals love the thick, flaky crusts and generous fillings. It’s the kind of place where you can chat with the baker while your pie cools on the rack. Authentic, homemade, and completely charming.
8. A-Frame Bakery – Williamstown
Nestled in the northern hills of the Berkshires, A-Frame Bakery is a hidden treasure. This spot specializes in hearty, rustic pastries made with local ingredients.
Their pies range from classic apple to unique options like maple-walnut and pear-ginger. Each crust is handmade and perfectly golden.
The bakery’s cozy wooden interior and friendly owners give it an old-fashioned vibe. Students from Williams College and travelers alike flock here for a slice that tastes like pure comfort in pastry form.
9. Madeleine’s Patisserie & Café – Pittsfield
For a taste of France in the Berkshires, Madeleine’s Patisserie & Café delivers beautifully. Known for elegant pastries, this café also serves exquisite pies and tarts.
Expect classics like French apple tart, chocolate hazelnut pie, and lemon meringue. Each is baked to perfection, combining European technique with local flavor.
Inside, you’ll find soft lighting, the hum of espresso machines, and the scent of sugar and vanilla. It’s the perfect spot for an afternoon coffee and dessert break, or to pick up a pie that will impress at any gathering.
10. Klara’s Gourmet – Lee
Klara’s Gourmet may be known for cookies, but the pies are hidden treasures. This bakery produces old-world treats inspired by the owner’s European roots.
The crusts are rich and flaky, with fillings highlighting simple, seasonal ingredients like local apples and wild blueberries. Klara’s avoids artificial flavors, sticking to traditional recipes.
It’s a quiet shop, the kind you might drive past without noticing – until the scent of baking draws you in. Stop by for a pie, and you’ll understand why locals guard this place like a secret. It’s authentic, heartfelt baking at its finest.
11. Richmond Bakery – Pittsfield
Richmond Bakery is one of those unassuming spots that’s quietly served locals for decades. The pies here are traditional and deeply satisfying.
Apple, pecan, and blueberry lead the lineup, though special flavors rotate with the seasons. Everything is made from scratch, with buttery crusts and hand-spiced fillings.
The bakery’s atmosphere is pure small-town Americana – simple, friendly, and always warm. Locals stop in early for a slice and coffee, while visitors find it’s the perfect roadside stop. If you’re craving an honest, old-fashioned pie, Richmond Bakery is a sweet reminder of comfort food’s true essence.
12. Monterey General Store – Monterey
Monterey General Store is part café, part community hub, and part hidden pie haven. Dating back to the 18th century, it’s one of the oldest general stores in New England.
Homemade pies are baked fresh in-house, and the menu changes with the seasons. Enjoy a slice with coffee on the porch, overlooking the quiet village street.
There’s a nostalgic magic to the place – creaky floors, handwritten signs, and the smell of sugar and butter. Each pie feels personal, crafted with care and simple ingredients. For true Berkshire charm, this store’s pies are as authentic as it gets.
13. The Marketplace Café – Lee
The Marketplace Café offers a modern twist on the classic pie shop. Known for its farm-to-table sandwiches, it also serves an ever-changing rotation of pies.
Think apple crumb with cinnamon streusel or seasonal berry pies bursting with local fruit. The crusts are flaky and golden, while the fillings are rich.
The café’s stylish yet laid-back atmosphere makes it perfect for brunch or takeaway. Every pie is made fresh daily by local bakers who value quality and creativity. For visitors exploring downtown Lee, The Marketplace is the perfect place to end your day with a slice of something truly delicious.
