A go-to café in downtown Lenox serving great coffee, fresh pastries, and solid breakfast and lunch options. Known for its espresso drinks, baked goods, and creative sandwiches, it’s an easy stop before exploring town or heading out for the day. Grab a seat inside or enjoy outdoor seating when the weather’s nice—perfect for a relaxed morning or casual midday bite. 

A favorite for quick, casual go-to for fresh bagels, breakfast sandwiches, and coffee right in town. Perfect for grabbing something easy before a hike or heading out for the day. Heads up: their hours are a little unusual — they’re typically open in the morning and close early (around 1PM), so this is definitely a breakfast/lunch-before-lunch spot. 

A bright, laid-back café and bakery right in town that’s perfect for breakfast, brunch, or an easy lunch. Expect great coffee, fresh baked goods, and a solid menu of sandwiches, salads, and classic comfort staples. Go for the Eggs Benedict — it’s a standout and a great pick if you want something filling before a full day out in the Berkshires.

Start your day in the heart of Lenox with a stop at Lenox Coffee — a beloved local café serving up expertly roasted brews, espresso classics, and a selection of teas and baked treats. Locals and visitors alike love lingering on the porch or grabbing a cup to go as they explore the charming streets of Lenox and the nearby historic district. It’s a relaxed, welcoming spot to sip a cappuccino, latte, or cold brew before heading out to shops, galleries, or the Berkshires’ scenic spots. 

If you’re craving a classic diner breakfast (or a comfort-food lunch), Joe’s Diner is a local favorite worth the short drive from Lenox. Expect hearty portions, friendly service, and all the staples—think omelets, pancakes, crispy home fries, burgers, and bottomless coffee. Easy, casual, and perfect before a day of exploring the Berkshires. 

A beloved chef-driven restaurant in downtown Lenox known for its seasonally inspired New American cuisine and intimate atmosphere. The menu changes often to highlight fresh, local ingredients, making every visit feel special. Guests rave about creative dishes, thoughtful flavors, and a warm, welcoming vibe that’s great for a date night or memorable dinner. With attentive service and an ever-evolving selection of small plates and entrees, Cello is a standout choice in the Berkshires dining scene. 

 This isn’t your typical pizza joint — step inside and you’ll immediately notice the funky, beach-shack vibe with colorful surf-inspired décor and casual seating that feels more fun than fancy. The real draw here? Big, delicious specialty slices with creative toppings and bold flavors that locals always rave about. Just a heads-up: it’s cash-only, so come prepared before you settle in for a slice (or two) of what many call some of the best pizza in the Berkshires. 

We wouldn’t be including this unassuming pho spot if we didn’t recommend it with all our heart — yes, it might seem a little out of the ordinary for the Berkshires, but it’s that good. Tucked just off the main road, Amazing Pho serves rich, flavorful bowls of pho and other Vietnamese favorites that locals rave about. Whether you’re craving a steamy bowl on a chilly day or something fresh like banh mi or spring rolls, this cozy, casual spot delivers big taste with friendly service. Great for lunch, dinner, or a casual bite between adventures. 

A short drive from Lenox, this chef-driven gastropub in a converted train depot is a local favorite for relaxed yet elevated dining. The warm, stylish interior and thoughtful menu — refreshed regularly with seasonal and globally inspired dishes — make it great for date nights, dinners with friends, or special occasions. Think creative entrees like short ribs, seared scallops, risotto, and hearty pub favorites paired with great cocktails and attentive service. It’s worth a reservation if you can swing it! 

Just a scenic drive from Lenox, Hilltown is a standout pizza destination that feels like a love letter to Italy right here in the Berkshires. Housed in a beautifully restored building with cozy, art-filled interiors and warm, relaxed vibes, this spot specializes in wood-fired, sourdough-style pies loaded with thoughtful, flavorful toppings — from delicately balanced classics to creative seasonal specialties. Whether you’re sharing a pizza with friends or savoring a glass of wine alongside locally sourced ingredients, Hilltown’s joyful hospitality and authentic Italian inspiration make it worth the journey. 

A lively, chef-driven American eatery and gastropub in downtown North Adams with a menu focused on fresh, seasonal ingredients and bold flavors. Locals and visitors love its inventive takes on classic dishes—from burgers and flatbreads to seasonal small plates—plus a strong rotating draft beer list, curated wines, and creative cocktails. The relaxed, modern atmosphere makes it a great stop for lunch or dinner after exploring nearby MASS MoCA or wandering the Berkshires. 

A classic Berkshires stop and a favorite with families. This working dairy farm is home to Jersey cows you can actually meet and pet, making it a fun, low-key outing for kids (and adults). Don’t skip the farm store—everything from the milk and cheese to the ice cream is made right on site, and it’s some of the best around. Easy to pair with a scenic drive or a quick afternoon stop. 

A must-stop sweet treat spot after a day of adventure. This local favorite serves up warm, hand-rolled dough cones filled with creamy soft-serve and your choice of toppings—think classic swirls, fun flavors, and lots of customizable goodness that keeps both kids and adults smiling.

Balderdash Cellars is a small-batch winery in the Berkshires known for great wine, scenic views, and an easygoing, social vibe. Balderdash offers a rotating lineup of thoughtfully made wines in a relaxed tasting room with both indoor and outdoor seating. Weekends often feature live music or visiting food trucks, making it an ideal stop for a laid-back afternoon of wine and mountain views.