TOP 30 Charming establishment in Pittsfield, Massachusetts

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Jae's at the Hilton Garden Inn is a charming restaurant located at 1032 South Street in Pittsfield, Massachusetts. This cozy establishment offers a warm and inviting atmosphere, perfect for enjoying a delicious meal with friends and family. With a diverse menu featuring a variety of culinary delights, guests can indulge in freshly prepared dishes made with the finest ingredients. Whether you're in the mood for a hearty breakfast, a light lunch, or a satisfying dinner, Jae's has something for everyone. Come and experience exceptional hospitality and mouthwatering cuisine at Jae's at the Hilton Garden Inn.

Berkshire Mountain Bakery Pizza Cafe is a charming establishment located at 180 Elm Street in Pittsfield, Massachusetts. This unique institution offers a delightful combination of bakery, cafe, food, restaurant, and store all in one convenient location. At Berkshire Mountain Bakery Pizza Cafe, customers can enjoy freshly baked breads, pastries, and pizzas made with locally sourced ingredients. The cozy cafe atmosphere invites guests to relax and savor their delicious meals while browsing the selection of artisanal products available for purchase.

East Side Cafe is a charming restaurant located at 378 Newell Street in Pittsfield, Massachusetts. Known for its cozy atmosphere and delicious food, this cafe offers a diverse menu featuring a variety of dishes to satisfy any palate. Whether you're in the mood for a hearty breakfast, a light lunch, or a satisfying dinner, East Side Cafe has something for everyone. Stop by and enjoy a meal in this welcoming establishment that is sure to become a favorite dining spot in the community.

Hotel on North is a charming and sophisticated institution located in the heart of Pittsfield, Massachusetts. Situated at 297 North Street, this unique establishment offers a combination of luxurious lodging, a vibrant bar, and a lively night club all under one roof. Guests can enjoy stylish accommodations, delicious cocktails, and exciting entertainment all in one convenient location. Whether you're looking for a relaxing retreat or a fun night out, Hotel on North has something for everyone. Experience the best of Pittsfield at this one-of-a-kind destination.

The Berkshire Inn is a charming lodging establishment located at 150 West Housatonic Street in the picturesque town of Pittsfield, Massachusetts. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests to enjoy during their stay. Conveniently situated in the heart of the Berkshires, guests can easily explore the area's many attractions, including cultural venues, outdoor activities, and charming shops and restaurants. Whether visiting for business or pleasure, the Berkshire Inn is the perfect home away from home for travelers seeking a relaxing and enjoyable experience in the beautiful Berkshires region.

Yankee Inn, Trademark Collection by Wyndham is a charming lodging establishment located at 461 Pittsfield Road in Lenox, Massachusetts, United States. This cozy inn offers comfortable accommodations and top-notch amenities, making it the perfect place to relax and unwind during your stay in the beautiful Berkshires. With its convenient location and warm hospitality, Yankee Inn is the ideal choice for travelers looking for a memorable and enjoyable experience in Lenox.

Knights Inn Lenox is a charming lodging establishment located at 474 Pittsfield Road in Pittsfield, Massachusetts. This cozy inn offers comfortable accommodations and excellent service to ensure a pleasant stay for guests. Conveniently situated in the heart of the Berkshires, guests can easily explore the area's attractions, including Tanglewood, Norman Rockwell Museum, and the beautiful landscapes of the region. With its affordable rates and welcoming atmosphere, Knights Inn Lenox is the perfect choice for travelers looking for a relaxing retreat in western Massachusetts.

Berkshire Yankee Suites is a charming lodging establishment located at 20 West Housatonic Street in the picturesque city of Pittsfield, Massachusetts. Our suites offer a cozy and comfortable stay for travelers looking to explore the beautiful Berkshire region. Each suite is tastefully decorated and equipped with modern amenities to ensure a relaxing stay. Our convenient location allows guests easy access to local attractions, dining options, and outdoor activities. Whether you are visiting for business or pleasure, Berkshire Yankee Suites is the perfect home away from home in the heart of the Berkshires.

Chez Pet is a charming store located at 55 Pittsfield Road in Lenox, Massachusetts. This pet-friendly establishment offers a wide range of products and services for your beloved furry friends. From premium pet food and toys to stylish accessories and grooming supplies, Chez Pet has everything you need to keep your pets happy and healthy. The knowledgeable and friendly staff are always ready to assist you in finding the perfect items for your pets. Visit Chez Pet today and treat your pets to the best in pet care!

Thistle & Mirth is a cozy and inviting bar and restaurant located at 44 West Street in Pittsfield, Massachusetts. This charming establishment offers a warm and welcoming atmosphere where guests can enjoy delicious food and drinks in a relaxed setting. With a menu featuring a variety of mouth-watering dishes and a wide selection of craft beers and cocktails, Thistle & Mirth is the perfect spot for a casual meal with friends or a night out on the town. Whether you're looking for a quick bite to eat or a leisurely dinner, this hidden gem in Pittsfield has something for everyone to enjoy.

Jae's 7 Winter is a cozy and inviting restaurant located at 7 Winter Street in the heart of Pittsfield, Massachusetts. Specializing in delicious comfort food and warm hospitality, this eatery offers a diverse menu of hearty dishes that are perfect for the winter season. Whether you're craving a steaming bowl of soup, a hearty sandwich, or a comforting plate of pasta, Jae's 7 Winter has something for everyone. Come in from the cold and enjoy a satisfying meal in a welcoming atmosphere at this charming establishment.

Epworth Arms is a welcoming institution located at 350 West Street in Pittsfield, Massachusetts. This cozy establishment offers comfortable accommodations and a friendly atmosphere for guests looking to relax and unwind. With its convenient location in the heart of Pittsfield, guests can easily explore the nearby attractions and enjoy all that this charming town has to offer. Whether you are visiting for business or pleasure, Epworth Arms provides a peaceful retreat for a memorable stay in the United States.

Red Light Hotel is a charming lodging establishment located at 218 Fourth Street in the heart of Pittsfield, Massachusetts. This cozy hotel offers comfortable accommodations with a touch of vintage charm. The rooms are tastefully decorated and equipped with modern amenities to ensure a pleasant stay for guests. Conveniently situated near the city's attractions, restaurants, and shops, Red Light Hotel is the perfect choice for travelers looking for a relaxing and enjoyable experience in Pittsfield. Whether you're visiting for business or pleasure, you'll feel right at home at this welcoming hotel.

Zucco's Family Restaurant is a charming dining establishment located at 451 Dalton Avenue in Pittsfield, Massachusetts. This beloved eatery is known for its warm and inviting atmosphere, delicious homemade Italian cuisine, and friendly service. Whether you're craving classic pasta dishes, mouthwatering pizzas, or savory seafood entrees, Zucco's has something to satisfy every palate. Bring your loved ones and enjoy a memorable dining experience at Zucco's Family Restaurant.

101 Restaurant & Bar is a vibrant establishment located at 1 West Street in Pittsfield, Massachusetts. This popular spot offers a unique blend of delicious food, refreshing drinks, and a welcoming atmosphere. Whether you're looking for a casual meal with friends or a night out on the town, 101 Restaurant & Bar has something for everyone. With a diverse menu featuring both classic favorites and innovative dishes, as well as a well-stocked bar serving up cocktails, beer, and wine, this is the perfect place to unwind and enjoy a great meal in a lively setting. Come experience the charm and hospitality of 101 Restaurant & Bar today!

RJ's Restaurant offers a delectable menu featuring a variety of seafood, chops, and pasta dishes. Located at 109 First Street in Pittsfield, Massachusetts, this cozy establishment is a must-visit for food enthusiasts looking to indulge in delicious and satisfying meals. Whether you are craving fresh seafood, juicy chops, or flavorful pasta, RJ's Restaurant has something for everyone. With a warm and inviting atmosphere, friendly staff, and top-notch service, dining at RJ's is sure to be a memorable experience. Come and enjoy a mouthwatering meal at this charming restaurant in the heart of Pittsfield.

Soda Chef is a charming restaurant located at 161 North Street in Pittsfield, Massachusetts. This unique establishment specializes in creating delicious and innovative soda flavors, perfect for pairing with their tasty menu offerings. From classic favorites to creative concoctions, Soda Chef offers a refreshing and fun dining experience for all ages. Come visit us and indulge in our handcrafted sodas and mouthwatering dishes in a cozy and welcoming atmosphere.

Thrive Diner is a charming restaurant located at 145 Wahconah Street in Pittsfield, Massachusetts. This cozy eatery offers a menu full of delicious and nutritious dishes that are sure to satisfy any appetite. From hearty breakfast options to savory lunch and dinner entrees, Thrive Diner is dedicated to providing fresh, locally sourced ingredients in every meal. Whether you're a vegan, vegetarian, or meat lover, there is something for everyone at this welcoming establishment. Come and enjoy a meal at Thrive Diner and experience the flavors of Pittsfield in every bite.

Angelina's is a charming institution located at 97 West Housatonic Street in Pittsfield, Massachusetts. This cozy spot offers a variety of delicious food options for takeout, dining in, or shopping in their store. From freshly prepared meals to gourmet snacks and specialty items, Angelina's has something for everyone. Stop by and experience the warm atmosphere and mouthwatering flavors that make this establishment a favorite among locals and visitors alike.

The Marketplace Cafe, located at 53 North Street in Pittsfield, Massachusetts, is a charming cafe and restaurant that also offers meal takeaway and specialty food items. Known for their Carvery Night featuring Roast Rib of Beef and other delicious dishes, the cafe is a popular spot for both locals and visitors. With a holiday wine list featuring a variety of options, as well as a selection of white and red wines available for purchase by the case or by the bottle, the Marketplace Cafe is the perfect place to enjoy a meal and a glass of wine. Established in 1993, Marketplace Catering, the parent company of the Marketplace Cafe, is known for their professionalism, quality, and personalized service. From signature sandwiches to oven-baked flatbread pizzas and hand-tossed salads, there is something for everyone to enjoy at the Marketplace Cafe. Whether you are looking for a quick bite to eat or planning a special event, the Marketplace Cafe has you covered. Open Monday through Friday from 7 am to 3 pm, Saturday from 8 am to 3 pm, and Sunday from 9 am to 2 pm, the Marketplace Cafe is a must-visit destination in the Berkshires.

Elm St Java is a cozy and inviting café located at 214-216 Elm Street in Pittsfield, Massachusetts. This charming establishment offers a wide variety of delicious coffee drinks, pastries, and light bites for patrons to enjoy. Whether you're looking for a quick pick-me-up or a relaxing place to unwind, Elm St Java is the perfect spot. With its friendly staff and welcoming atmosphere, it's no wonder why this café has become a favorite among locals and visitors alike. Come stop by and experience the warm hospitality and tasty treats that Elm St Java has to offer.

Kelly's Diner is a charming and cozy restaurant located at 860 Dalton Avenue in Pittsfield, Massachusetts. This beloved establishment offers a classic diner experience with a menu full of delicious comfort food options. From hearty breakfast dishes to savory burgers and sandwiches, Kelly's Diner has something for everyone to enjoy. Whether you're a local looking for a favorite spot to dine or a visitor passing through town, Kelly's Diner is sure to satisfy your cravings and leave you feeling satisfied. Come on in and experience the warm hospitality and tasty dishes that make Kelly's Diner a must-visit destination in Pittsfield.

Bear Butter is a charming food store located at 381 Tyler Street in Pittsfield, Massachusetts. Specializing in gourmet butter products, this unique establishment offers a wide variety of artisanal butter spreads and flavored butters. From savory garlic and herb butter to sweet honey and cinnamon butter, Bear Butter has something to please every palate. Whether you're looking to elevate your cooking or simply enjoy a delicious spread on toast, this cozy store is sure to have just what you need. Visit Bear Butter today and experience the rich and creamy goodness for yourself.

Lulu's Tiny Grocery is a charming little food establishment located at 137 North Street in Pittsfield, Massachusetts. This hidden gem offers a unique dining experience with a focus on fresh, locally sourced ingredients. From gourmet sandwiches to artisanal cheeses, Lulu's has something for everyone. Come visit us and taste the difference at Lulu's Tiny Grocery!

Uncorked Wine & Beer Lounge is a cozy and inviting bar located at 137 North Street in Pittsfield, Massachusetts. This establishment offers a wide selection of wines and craft beers for guests to enjoy in a relaxed and laid-back atmosphere. Whether you're a wine connoisseur or a beer enthusiast, Uncorked has something for everyone. Come unwind and socialize with friends while sipping on your favorite beverage at this charming lounge.

Kirk's Variety & Hobby Center is a charming convenience store located at 784 Tyler Street in Pittsfield, Massachusetts. This family-owned establishment offers a wide range of products including snacks, beverages, groceries, and unique hobby supplies. Whether you're looking for a quick bite to eat, a last-minute gift, or supplies for your latest crafting project, Kirk's Variety & Hobby Center has you covered. Stop by today and experience their friendly service and diverse selection of goods.

The Burrow is a charming store located at 881 Dalton Avenue in Pittsfield, Massachusetts. This cozy establishment offers a unique selection of handmade goods, artisanal crafts, and vintage treasures. Visitors can browse through a variety of one-of-a-kind items, perfect for adding a touch of character to their homes or finding a special gift for a loved one. With its welcoming atmosphere and carefully curated collection, The Burrow is a must-visit destination for those seeking something truly special.

Old Soul Sounds is a charming institution located at 77 Seymour Street in Pittsfield, Massachusetts. This unique establishment is a haven for music lovers and vintage enthusiasts alike, offering a curated selection of vinyl records, turntables, and audio equipment. Step inside and you'll be transported to a bygone era, where the sound of crackling records fills the air and nostalgia reigns supreme. Whether you're a seasoned collector or a casual listener, Old Soul Sounds is sure to delight with its timeless offerings and welcoming atmosphere. Come visit us and discover the magic of music at this hidden gem in the heart of Pittsfield.

Sarah's Cheesecake & Cafe is a charming bakery and cafe located at 180 Elm Street in Pittsfield, Massachusetts. Our cozy establishment offers a wide variety of delicious cheesecakes, freshly baked pastries, and savory meals for dine-in or takeout. Whether you're looking for a quick bite to eat, a leisurely meal with friends, or a sweet treat to satisfy your cravings, Sarah's Cheesecake & Cafe has something for everyone. Come visit us today and indulge in our scrumptious offerings in a warm and inviting atmosphere.

Marie's North Street Eatery And Gallery is a charming restaurant located at 146 North Street in Pittsfield, Massachusetts. This unique establishment offers a delightful combination of delicious food and beautiful artwork, creating a warm and inviting atmosphere for guests to enjoy. Whether you're stopping by for a quick bite to eat or looking to explore local art, Marie's North Street Eatery And Gallery is the perfect destination for a memorable dining experience. So come visit us and indulge in a culinary and artistic delight at this hidden gem in the heart of Pittsfield.