Chocolate Springs Cafe

Frankie’s Ristorante Italiano is a beloved family-run gem delivering authentic Italian comfort in a cozy, bustling downtown spot, famed for its house-made red sauce, generous portions of classics like shrimp puttanesca,…

MacKimmie Co. is a refined home‑and‑lifestyle shop specializing in American‑ and European‑made textiles, apparel, and gifts, with a focus on luxurious wool and cashmere blankets, throws, sheets, and accessories that blend…

Shots Cafe is a cozy, European‑style café serving specialty coffee, espresso‑bar drinks, and a curated menu of breakfast and lunch items, including signature Eggs Benedict, hearty sandwiches, and fresh salads, all…

Twigs is a women’s fashion boutique offering a tightly edited selection of stylish, wear-everyday clothing and accessories that blend designer quality with a relaxed, “weekend‑in‑the‑Berkshires” feel. The shop, opened in 2003…

Artemesia is a small, locally owned women’s clothing boutique showcasing a quietly refined collection of handmade, small‑batch apparel and accessories designed for everyday ease and long‑term wear. The shop features soft,…

Fluff Alpaca is a family‑owned boutique that specializes in luxuriously soft alpaca clothing, accessories, and yarn for men, women, and children, with many pieces hand‑knit from fiber raised on the owners’…

Home Love is a cozy, locally beloved gift and home‑decor shop offering a thoughtfully curated mix of small‑batch and handmade goods, including jewelry, candles, host gifts, and seasonal home accents that…

One Mercantile is a small, thoughtfully curated home‑goods and gift boutique in the historic Marble Block section of downtown, steps from other popular shops and cafés. The store focuses on vintage‑inspired,…

Arcadian Shop is an independent outdoor specialty retailer serving as the Berkshires’ go‑to destination for bikes, kayaks, paddleboards, camping gear, hiking apparel, running and climbing footwear, and a broad range of…

Shooz is a specialty footwear and accessories boutique offering a fashion‑forward yet comfortable selection of shoes and complementary pieces for women who like individualized, well‑fitting styles. The store carries a mix…

Casablanca is a luxury fashion boutique offering a carefully edited mix of contemporary designer clothing, shoes, and accessories for women and men, with labels that include high‑end European and American brands…

Design Menagerie is a thoughtfully curated lifestyle boutique offering a tightly edited mix of home décor, clothing, wellness products, and artisanal gifts that emphasize “simple, useful, beautiful” objects made with an…

Wilcox & Co. is a boutique-style retail shop located in the heart of the Lenox village, offering a curated mix of gifts, home décor, and lifestyle goods tailored to visitors and…

GB9 is a contemporary clothing boutique offering a curated selection of women’s (and some men’s) fashion, footwear, and accessories in a compact, stylish downtown storefront that blends urban edge with a…

Lee Premium Outlets is a Simon‑owned open‑air shopping center designed to feel like a classic New England village and serving as a major retail destination at the gateway to the Berkshires,…

Salmon Run Fish House is a family‑owned seafood restaurant known for its welcoming, casual‑family atmosphere, fresh coastal‑style seafood, and a broad menu that also includes steaks, grilled chicken, and pasta, making…

Starving Artist Creperie & Cafe is a vibrant, locally owned spot established in 2011 within a restored 154-year-old historic building adjacent to the Good Purpose Gallery, specializing in freshly made sweet…

Mazzeo’s Ristorante is Pittsfield’s top-rated family-owned Italian gem since 1988, run by second-generation brothers Tony and Michael Mazzeo, delivering fine authentic cuisine with fresh seafood, homemade pasta, veal, eggplant specialties, and…

District Kitchen & Bar is an intimate contemporary American gastropub emphasizing seasonal, locally sourced fare prepared in-house by Executive Chef Taylor Hitchcock, featuring standout dishes like fried calamari with chipotle-ginger vinaigrette,…

Patrick’s Pub is a beloved Irish-American pub and restaurant in the heart of downtown, renowned for its homemade comfort food like Patrick’s Famous Hot Wings, New England Clam Chowder, juicy Patrick’s…

The Bistro Box is a beloved seasonal roadside eatery celebrated for classic American shack food with modern twists, featuring fresh homemade burgers like the signature Box Burger with tomato bacon jam,…

Barrington Brewery & Restaurant is a pioneering Berkshire brewpub established in 1995 as the East Coast’s first solar-powered brewery, crafting exceptional house ales and lagers like cask-conditioned favorites alongside scratch-made American…

The Prairie Whale is a celebrated farm-to-table gem in a charming historic house, helmed by owner Mark Firth (ex-Brooklyn’s Diner and Marlow & Sons) and Chef Dan Studwell, delivering nose-to-tail American…

Fuel Coffee Shop is a lively gourmet bistro and community hub offering all-day breakfast, brunch, and lunch fare like bacon-egg-cheese sandwiches, morning glory muffins, pancakes, fresh pastries, salads, and deli sandwiches…

GB Eats is a rejuvenated all-day diner transformed from the former Neighborhood Diner under Chef Pierre Cum and Candice Rischner, serving hearty American comfort food from breakfast through dinner, including eggs…

Antimony Brewing – Craft Brewery & Kitchen is a community brewpub featuring house-brewed craft beers from an onsite 7-barrel system visible through the taproom, paired with scratch-made comfort food like smash…

Nejaime’s Wine Cellars is a Berkshire staple with over 50 years of excellence as the premier fine wine and spirits merchant, boasting an extensive global selection of over 2,000 wines, craft…

Lenox Coffee is a charming, locally owned coffee shop housed in a quaint house with a welcoming porch, serving exceptional brews made from locally roasted beans, including smooth espresso drinks, lattes,…

Patisserie Lenox is a cherished French bakery established in 2011, renowned for its exquisite handmade pastries, macarons, specialty cakes, croissants, tarts, and éclairs alongside a daily lunch menu featuring quiches, croque…

Loeb’s Foodtown of Lenox is a family-owned neighborhood grocery cornerstone serving the Berkshires for over 40 years with fine essentials, including farm-fresh organic produce, premium meats from an expert butcher, coffee,…

Betty’s Pizza Shack is a laid-back, surf-shack-inspired eatery dishing up specialty pizzas like Surf the Goat and El Cholo alongside wings, burritos, quesadillas, chopped salads, sandwiches, and appetizers with fresh, wholesome…

The Olde Heritage Tavern is a longstanding local hangout since 2000 as “Lenox, Plain & Simple” for its cozy, lively pub atmosphere, dishing out hearty comfort fare like juicy burgers, crispy…

Brava is a Lenox dining mainstay since 2012, celebrated by Yankee Magazine as offering the “Best Small Plates” through its vibrant tapas-style menu of hot and cold shareables like gambas al…

Ombra is a cozy tapas and wine bar opened in early 2023 by the team behind Brava, offering shareable small plates like potato croquettes, fried calamari, olive feta, millionaire tots, arugula…

Pizzeria Boema is a chef-driven hotspot specializing in authentic Neapolitan-style wood-fired pizzas crafted in a blazing 900°F oven by trained pizzaiolo Roman from Frankie’s, featuring thoughtfully sourced ingredients like housemade mozzarella,…

Firefly Gastropub is a vibrant, welcoming gastropub delivering elevated comfort food with creative flair in a cozy, lively downtown setting, celebrated for standout dishes like tuna tartare, shrimp tempura, pan-seared sea…

Bagel & Brew is a quirky, beloved neighborhood spot blending fresh-boiled bagels, hearty breakfast sandwiches (like sausage-egg-cheese or BLT on everything bagels), cold brew coffee on tap, and simple cream cheese…

Alta Restaurant & Wine Bar is a top-rated upscale gem offering elevated Mediterranean-inspired cuisine in a cozy, elegantly understated downtown setting, renowned for its exceptional dishes like perfectly cooked beef tenderloin,…