🛒 Groceries
Whether you are stocking up for a week-long stay or grabbing supplies for a backyard barbecue, these are your primary stops.
- Guido’s Fresh Marketplace (10-15 Mins): The premier "foodie" destination. If you are planning a gourmet feast, head to their Lenox or Great Barrington locations for the region's best butcher cuts, fresh fish, local cheeses, and organic specialties.
- Big Y World Class Market (2 Mins): Your local Lee headquarters. Just down the road on Housatonic, this is your one-stop shop for massive grocery hauls, fresh produce, and all the group supplies you’ll need for the week. They also have convenient EV charging on-site!
Host Tip: Don't miss the Lee Farmers Market (Saturdays, Summer/Fall). It’s just a short, perfect Saturday morning stroll from our front door and the best place to pick up fresh berries, local honey, and artisanal g
🍷 Wine & Spirits
Pair your dinner, sunset cocktails, or lawn concert picnic with the perfect bottle. From rare, natural vintages to trusted staples for a Tanglewood spread, these local shops offer the finest selection in the county.
- Dare Bottleshop & Provisions (Lenox): A beautiful, family-owned boutique shop right in the heart of Lenox. Dare specializes in exceptional, small-production, low-intervention, and natural wines from around the world. It is also an absolute goldmine for unique craft beers, hard ciders, and high-end pantry goods like tinned fish and gourmet condiments—perfect for the culinary-curious traveler.
- Nejaime’s Wine Cellars (Lenox & Stockbridge Locations): A legendary Berkshire institution and a trusted staple for over 50 years. They boast a massive selection of fine wines, liquors, and craft brews across both locations. Bonus for guests: They are famous for their artisanal cheese stations and custom, specialty picnic spreads that have won regional awards specifically for being perfect for Tanglewood.
- Spirited Wines (Lenox): Located on Pittsfield Road, this premier shop offers an incredible, global selection of wines, rare gems, and discount liquors. Beyond the bottle, they feature an excellent spread of artisanal cheeses and specialty foods. They even offer custom, themed charcuterie and picnic boxes designed to grab and go on your way to a concert or hike.
🧀 Cheese, Dairy & Ice Cream
Elevate your pre-concert charcuterie board or satisfy your late-night sweet tooth with spectacular regional dairy. While you can find an exceptional selection of fine cheeses tucked away inside Guido’s Marketplace, Dare Bottleshop, Nejaime’s, and Spirited Wines, these destinations are well worth a dedicated trip.
- High Lawn Farmstead Creamery (Lee): An absolute must-visit right here in town. This historic Jersey dairy farm produces world-class, artisan cheeses, rich farm-fresh milk, and incredible small-batch ice cream. Take a stroll through the barns to see the calves between 10:00 AM and 4:00 PM, then pop into their Creamery Shop to stock your cooler with award-winning cheeses and grab a scoop of their signature ice cream.
- Lucky’s Ice Cream (Lee): A fantastic, ultra-convenient spot right down the road in Lee. Perfect for families, Lucky's features a massive variety of hard and soft-serve flavors (including great dairy-free and vegan options) and a small playground out back for the kids. It’s a nostalgic, high-energy neighborhood staple with incredibly generous portion sizes.
- Berkshire Cone (Lenox): A wonderful, classic walk-up window right in downtown Lenox that serves up fantastic ice cream and treats. It’s a perfect post-dinner stop during a summer stroll through the village. Local Note: This is a seasonal gem, so keep in mind they are closed during the winter months.
- SoCo Creamery (Great Barrington): A legendary Berkshire staple. Known for their super-premium, micro-batch ice cream, SoCo uses simple, delicious ingredients to craft dense, incredibly flavorful scoops. Pop into their bustling Great Barrington scoop shop for classic favorites or innovative seasonal flavors.
- Ella Mae’s (West Stockbridge): A delightful, picture-perfect little village ice cream spot. It’s the ultimate place to swing by after a walk through downtown West Stockbridge or an afternoon spent wandering the nearby art galleries. Grab a cone and enjoy the beautiful local town vibe.
- Rubiner’s Cheesemongers & Grocers (Great Barrington): A culinary landmark set inside a grand historic bank building. Run by one of the country's most respected cheesemongers, this shop features an impeccably sourced selection of rare artisan cheeses, cured meats, and international dry goods. It is the ultimate playground for building a museum-quality picnic spread.
Explore more insider favorites on the Berkshire Blog