Dog Friendly Restaurants in Windsor, MA

There are 53 dog-friendly restaurants within 40 kilometers of Windsor that welcome dogs at their outdoor tables. Need help to decide where to eat? Here’s a detailed description of each restaurant, along with pictures and reviews from other dog owners. Coming from out of town? Get a discounted rate on pet friendly hotels in Windsor. Bone appetit!

The Purple Pub

Williamstown, MA

The Purple Pub Dogs are welcome at more than five umbrella-covered outdoor tables at this Williamstown pub. The Purple Pub is a good spot to grab a bite and a brew. Choose from one of the 24 draft beers on tap, then choose from a selection of appetizers, sandwiches, salads, and burgers. Good grub choices include Southwestern turkey chili, Guinness BBQ chicken wings, fried pickles with ranch dressing, quinoa salad, BLTA sandwich, buffalo chicken panini, lobster club wrap, and a cheddar cheese burger topped with thousand island dressing. See Details

Tunnel City Coffee

Williamstown, MA

Tunnel City Coffee Dogs are welcome at ten outdoor tables along the sidewalk at Tunnel City Coffee in Williamstown, MA. This pet-friendly coffee shop serves freshly-roasted coffee alongside slices of quiche, cake, bagels, chocolate peanut butter pie, iced cookies, muffins, coffee cake, and scones. Fido must remain outside while you go in to order. See Details

No. Six Depot Roastery & Cafe

West Stockbridge, MA

No. Six Depot Roastery & Cafe No. Six Depot Roastery & Cafe is a coffeehouse in West Stockbridge, MA, with dog-friendly table outside. They serve breakfast and lunch daily alongside fresh roasted coffee and espresso drinks. Try the Belgian waffles topped with Nutella, bananas and berries for a sweet start to the day. In the mood for something savory for breakfast? Order scrambled eggs and thick-cut smokehouse bacon with buttery grilled Berkshire Mountain toast. Panini sandwiches, salads and soups are available for lunch. See Details

Ben & Jerry's

Pittsfield, MA

Ben & Jerry's Ben and Jerry's is a dog-friendly frozen sweet shop serving, 'fresh and extraordinary dairy,' to Pittsfield locals and tourists alike. Dog owners can head to one of Ben and Jerry's four outdoor tables to indulge in the sunshine alongside their furry friend. The shop's menu includes flavors such as Bourbon Brown Butter, Cherry Garcia, Empower Mint, Phish Food, Totally Baked, and The Tonight Dough. Its menu also includes an array of cones, sundaes, smoothies, and shakes. Please note that table service isn't available, so your dog will need to be tied up outside while you go in to order. See Details

Haven Cafe & Bakery

Lenox, MA

Haven Cafe & Bakery Dogs are welcome at six outdoor tables at this bakery cafe. Haven Cafe & Bakery serves breakfast, weekend brunch, and lunch. Menu items include the breakfast burrito, croissant French toast, burger topped with Spanish blue cheese and roasted mushrooms, curry chicken salad, and grilled polenta. Haven Cafe & Bakery is open Monday - Friday 7:30am - 3pm, Saturday - Sunday 8am - 3pm. See Details

Starving Artist Cafe and Creperie

Lee, MA

Starving Artist Cafe and Creperie Dogs are welcome at two outdoor tables at this cute cafe. Starving Artist Cafe serves sweet and savory crepes, panini sandwiches, soups, salads and baked goods, organic fair-trade pour-over and drip coffee, organic teas, and other gourmet foods using quality local and organic ingredients. Starving Artist Cafe is open Monday, Wednesday, Thursday 7:30am - 3:30pm, Friday - Saturday 7:30am - 5pm, Sunday 7:30am - 2pm. See Details

Berkshire Pizzeria

Charlemont, MA

Berkshire Pizzeria Dog-friendly Berkshire Pizzeria welcomes Fido at outdoor table on their covered deck with relaxing river and mountain views in Charlemont, MA. They use fresh and quality ingredients, most of which are imported weekly including bread from Brooklyn. Enjoy New York style thin crusts pizzas with a wide variety of toppings. Their menu also includes fully loaded grinders, house made Empanadas, and award winning chili. See Details

Ramuntos Brick Oven Pizza

North Adams, MA

Ramuntos Brick Oven Pizza Ramuntos Brick Oven Pizza is a dog-friendly pizzeria in North Adams, MA where Fido is welcome to join you on the sidewalk seating. Try their New York style specialty pizza, Sicilian style pizza, or a hoagie when you're visiting! Don't forget to check out their extensive beer menu. See Details

Bagel & Brew

Lenox, MA

Bagel & Brew Bagel & Brew is a dog-friendly bagel shop and beer garden in Lenox, MA. Fido is welcome to join you at picnic table seating in the beer garden. Try their delicious deli sandwiches like the Super Nova, New Yorker, or Blazin' Buffalo, or grab a fresh bagel with a craft beer or kombucha on tap! See Details

Craft Food Barn

North Adams, MA

Craft Food Barn Craft Food Barn is a pet-friendly restaurant serving the northern Berkshires in North Adams, MA. Fido is welcome to chow down with you at one of the outside tables. Guests can order by drive through or walk in, but dogs must remain outside. The menu has a variety of options, including burgers, sandwiches, acai bowls, ice cream and more. See Details

The Olde Heritage Tavern

Lenox, MA

The Olde Heritage Tavern The Olde Heritage Tavern is a pet-friendly restaurant in charming downtown Lenox, MA. Fido can join you while you eat outside at one of the six umbrella-covered tables on the front patio. The menu features salads, wings, quesadillas, wraps, burgers, and traditional pub fare like the open-faced tuna melt, fish and chips, and chicken parmesan. See Details

'6 House Pub

Williamstown, MA

'6 House Pub Dogs are welcome on the patio outside '6 House Pub in Williamstown, MA. This pet-friendly eatery offers a variety of dishes including lobster rolls, crab cakes, burgers, shrimp scampi and lobster mac & cheese. They serve craft beer and creative cocktails, and have vegetarian and gluten-free options available. Make sure to order from the dog menu which features bark balls, chicken a la hound and chilly paws! See Details

The Farmstead Creamery Shop at High Lawn Farm

Lee, MA

The Farmstead Creamery Shop at High Lawn Farm The Farmstead Creamery Shop is a pet-friendly eatery at High Lawn Farm in Lee, MA. Four-legged friends are invited to join you for a visit at this local shop for a delicious pup cup! Unwind at one of their picnic tables while treating yourself to farm-fresh ice cream with seasonal flavors. While table service isn't provided, they have a walk-up window, making it convenient to order while Fido stays by your side. See Details

Once Upon a Table

Stockbridge, MA

Once Upon a Table Once Upon a Table is a fine dining farm-to-table establishment, offering seasonal, locally-sourced dishes on a menu updated daily. Located in Stockbridge, MA, this dog-friendly restaurant welcomes pups at their front patio tables when the weather is nice. Dine on their rotating menu of unique dishes, such as curry potato & cauliflower soup, wild mushroom polenta, jacuterie chorizo sandwich, and more. See Details

Avocado Cafe Lee

Lee, MA

Avocado Cafe Lee Avocado Cafe Lee is a pet-friendly restaurant in Massachusetts. Fido is welcome to join you at an outdoor table while you try their local, fresh take on Mexican dishes. Sides include pico de gallo, guacamole and french fries. See Details

Carm’s Restaurant and Coffee Shop

Chester, MA

Carm’s Restaurant and Coffee Shop Carm's Restaurant and Coffee Shop is a dog-friendly breakfast and lunch restaurant where your leashed dog is welcome to join you at a table on the outdoor patio. Serving everything from classics like corned beef hash to cinnamon rolls and flatbread pizzas, you are sure to find your new favorite here! See Details

Let's do Lunch

Lee, MA

Let's do Lunch Bring Fido to sit outside with you at a pet-friendly bistro-style table on the sidewalk in front of Let's Do Lunch. This restaurant in Lee, MA, serves fresh salads, soup and sandwiches in the afternoon. You won't want to miss out on trying their house-specialty Maine lobster roll! See Details

Brava

Lenox, MA

Brava Brava is a dog-friendly eatery in Lenox, MA, where Fido can join you at an outdoor table on the covered patio. The menu features tapas, pizzas, and cheese plates. See Details

Burmese Bowl

Lee, MA

Burmese Bowl Burmese Bowl, located in Lee, MA, is a pet-friendly spot where your leashed furry friend can join you on their outdoor covered porch. The restaurant has a diverse menu featuring fresh salads, flavorful noodles and delicious sushi. Don't miss out on their delightful mochi for dessert. Plus, vegan options are available, ensuring that everyone in your party can find something they love. See Details

Patisserie Lenox

Lenox, MA

Patisserie Lenox Dogs are welcome at five outdoor tables at this bakery serving gourmet coffees and teas, homemade ice cream, French breakfasts, and organic lunches. Patisserie Lenox's menu includes chocolate eclairs, croissants, cinnamon puff pastry twists, beet and goat cheese salad, brie and raspberry croissant sandwiches, slices of ham and swiss quiche, soups, Caprese salads, and Croque Madame sandwiches. Patisserie Lenox is open daily from 9am until 6pm or 7pm; hours vary seasonally. See Details