TOP 30 Best Night out in Pittsfield, Massachusetts

The Pittsfield CityJazz Festival has been a staple of jazz performance and education in the Berkshires since 2005. Located at 111 South Street in Pittsfield, Massachusetts, this institution offers a variety of events over 11 days, including Swing Dance, Jam Sessions, an Annual Jazz Crawl, Jazz Prodigy Concerts, Jazz Brunches, and performances by world-renowned headliners. One of the festival's highlights is "10 by Duke", an exploration of Duke Ellington's music. Taking place on Saturday, February 24th at 7:30pm at the Berkshire Museum, this event celebrates the 125th birthday of the legendary composer. Fifty years after his passing, Duke Ellington is still considered America's most prolific composer, and this concert will showcase 10 of his most renowned and familiar works. The artists performing in this Ellington anthology include The Hot Club of New England. Don't miss out on this special event as part of Pittsfield's annual 10x10 Upstreet Winter Arts Festival.

Welcome to Pittsfield Station, your premier parking destination conveniently located at 1 Columbus Avenue in the heart of Pittsfield, Massachusetts. We offer a safe, secure, and spacious parking facility designed to meet the needs of both daily commuters and visitors to the area. Whether you're heading to work, exploring the charming local attractions, or enjoying a night out, Pittsfield Station provides easy access and peace of mind with our well-maintained parking spaces. Our facility is equipped with state-of-the-art security features, including surveillance cameras and well-lit areas, ensuring the safety of your vehicle. We offer competitive rates and flexible parking options to accommodate your schedule, whether you need short-term parking or a more extended stay. Our friendly staff is always on hand to assist with any questions or concerns, making your parking experience as seamless as possible.

Welcome to Black Luxe Limousine Service, your premier choice for luxury transportation in Pittsfield, Massachusetts. Conveniently located at 555 East Street, we specialize in providing an exceptional travel experience tailored to both personal and corporate needs. Whether you're planning a special night out, a corporate event, or need airport transportation, our fleet of elegant limousines and professional chauffeurs are here to ensure a smooth and stylish journey. At Black Luxe Limousine Service, we pride ourselves on delivering unparalleled customer service and attention to detail, making every ride with us a memorable one. Our vehicles are meticulously maintained and equipped with state-of-the-art amenities to offer you the utmost comfort and sophistication. We understand the importance of punctuality and reliability, and our team is committed to exceeding your expectations every time you choose us.

The Colonial Theatre, located at 111 South Street in Pittsfield, Massachusetts, is a historic performing arts venue that has been entertaining audiences since 1903. This beautifully restored theater features a variety of live performances including Broadway shows, concerts, dance performances, and film screenings. With its stunning architecture and state-of-the-art facilities, the Colonial Theatre offers a unique and unforgettable experience for theatergoers of all ages. Don't miss the opportunity to catch a show at this iconic institution in the heart of the Berkshires.

Sibaritas is a renowned restaurant located at 1264 East Street in Pittsfield, Massachusetts. Known for its exquisite and innovative cuisine, Sibaritas offers a unique dining experience that combines traditional flavors with modern techniques. The restaurant prides itself on using only the freshest ingredients sourced locally to create dishes that are both delicious and visually stunning. Whether you're looking for a romantic dinner for two or a special celebration with friends and family, Sibaritas is the perfect choice for a memorable dining experience.

Teddy's Pizza Inc. is a beloved family-owned restaurant nestled in the heart of Pittsfield, Massachusetts. We take pride in upholding traditional pizza-making techniques, using only the finest ingredients, and providing a warm and inviting atmosphere for our community. Whether you're craving a classic slice or looking to host a special event, Teddy's Pizza has you covered. Our hours of operation are Monday to Saturday from 11 am to 9 pm, with Wednesdays and Sundays being our days of rest. For inquiries about our special event services, please reach out to us at teddyspizza413@gmail.com. Come join us at 508 East Street for a memorable dining experience at Teddy's Pizza Inc.

Methuselah Bar and Lounge is a vibrant and stylish establishment located at 391 North Street in Pittsfield, Massachusetts. This multifaceted venue offers a unique blend of bar, food, night club, and restaurant experiences all under one roof. Whether you're looking to enjoy craft cocktails with friends, indulge in delicious gourmet cuisine, dance the night away to live music, or simply unwind in a chic and welcoming atmosphere, Methuselah Bar and Lounge has something for everyone. Come and experience the ultimate night out in Pittsfield at Methuselah Bar and Lounge.

K&M Bowling is a popular bowling alley located at 555 Dalton Avenue in Pittsfield, Massachusetts. This family-friendly establishment offers a fun and exciting atmosphere for bowlers of all ages and skill levels. With a variety of lanes, arcade games, and a snack bar, K&M Bowling is the perfect place to host a birthday party, corporate event, or simply enjoy a night out with friends. Whether you're a seasoned pro or a beginner looking to improve your game, K&M Bowling has something for everyone. Come visit us and experience the thrill of knocking down pins in a lively and welcoming environment.

Teo's is a charming restaurant located at 1410 East Street in Pittsfield, Massachusetts. Known for its delicious food and welcoming atmosphere, Teo's offers a diverse menu featuring a variety of dishes to satisfy all tastes. Whether you're craving classic American comfort food or international cuisine, Teo's has something for everyone. With friendly staff and a cozy ambiance, Teo's is the perfect spot for a casual meal with friends or a special night out. Come visit us at Teo's and experience the flavors of Pittsfield!

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.

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.

Phoenix Theatres Beacon Cinema, located at 57 North Street in Pittsfield, Massachusetts, is a state-of-the-art movie theater that offers a luxurious and immersive cinematic experience. With the highest quality picture image, wall-to-wall screen, and cutting-edge sound system, Phoenix Theatres sets a new standard in sight and sound. Guests can enjoy the latest sound phasing technology, trinnov, which enhances the audio experience with unparalleled clarity and depth. In addition to the exceptional audiovisual experience, Phoenix Theatres Beacon Cinema offers heating reclining loveseat style pods with power reclining features, allowing guests to relax in ultimate comfort while watching their favorite films. The theater also serves alcohol at all locations, including a stellar selection of domestic beer, craft beer, and red & white wine.

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!

Located at 342 Merrill Road in Pittsfield, Massachusetts, O'Laughlin's Pub is a cozy and inviting bar where locals and visitors alike come to unwind and enjoy a great atmosphere. With a wide selection of beers on tap, signature cocktails, and delicious pub fare, O'Laughlin's Pub is the perfect spot to catch up with friends or watch the game. The friendly staff and warm, welcoming ambiance make it a favorite hangout for those looking for a laid-back night out. Whether you're looking to relax after a long day or celebrate a special occasion, O'Laughlin's Pub has something for everyone.

Vong's Thai Cuisine is a popular restaurant located at 157 Seymour Street in Pittsfield, Massachusetts. Known for its authentic Thai dishes and flavorful cuisine, Vong's offers a wide variety of dishes that are sure to satisfy any craving for Asian cuisine. With a cozy and inviting atmosphere, this restaurant is the perfect spot for a casual meal or a special night out. Whether you're a fan of spicy curries, flavorful stir-fries, or refreshing noodle dishes, Vong's Thai Cuisine has something for everyone. Come visit us and experience the taste of Thailand right here in the heart of Pittsfield.

The Italian-American Club is a popular bar located at 203 Newell Street in Pittsfield, Massachusetts. This vibrant institution celebrates the rich cultural heritage of Italian-Americans through delicious food, refreshing drinks, and a welcoming atmosphere. Join us for a taste of Italy right here in the United States, where you can enjoy traditional Italian cuisine, sip on classic cocktails, and socialize with friends and family. Whether you're looking for a casual night out or a lively gathering, the Italian-American Club is the perfect spot to relax and enjoy the company of others. Come experience the warmth and hospitality of our establishment today!

Cim's Tavern is a cozy and inviting bar located at 429 Fenn Street in Pittsfield, Massachusetts. Known for its friendly atmosphere and great drinks, Cim's Tavern is a popular spot for locals and visitors alike. Whether you're looking to relax with a cold beer after work or catch up with friends over cocktails, Cim's Tavern has something for everyone. With a diverse selection of beers, wines, and spirits, as well as tasty bar snacks, it's the perfect place to unwind and enjoy good company. Stop by Cim's Tavern and experience the laid-back charm of this neighborhood bar.

Sideline Saloon is a lively bar located at 434 Fenn Street in Pittsfield, Massachusetts. Known for its welcoming atmosphere and friendly staff, this popular establishment offers a wide range of drinks, including craft beers, cocktails, and spirits. Guests can enjoy watching sports games on big-screen TVs, playing pool or darts, and socializing with friends. With regular live music events and special promotions, Sideline Saloon is the perfect spot for a fun night out in Pittsfield.

Parkside is a cozy and inviting bar, food, and restaurant located at 220 West Housatonic Street in Pittsfield, Massachusetts. This institution offers a welcoming atmosphere where guests can enjoy delicious food, refreshing drinks, and great company. Whether you're looking for a casual meal, a night out with friends, or a place to unwind after a long day, Parkside has something for everyone. With its convenient location and friendly staff, Parkside is the perfect spot to relax and enjoy a memorable dining experience in the heart of Pittsfield.

110 Grill Lenox is a popular restaurant located at 489 Pittsfield Road in Lenox, Massachusetts. Known for its diverse menu and inviting atmosphere, this establishment offers a wide range of delicious dishes to satisfy every palate. Whether you're in the mood for a juicy burger, fresh seafood, or a hearty pasta dish, 110 Grill Lenox has something for everyone. With friendly service and a warm ambiance, this restaurant is the perfect spot for a casual lunch, a special dinner, or a celebratory meal with friends and family. Experience the flavors of Lenox at 110 Grill.

New Asian Garden is a popular restaurant located on Newell Street in Pittsfield, Massachusetts. This delightful eatery offers a wide range of delicious Asian cuisine, including Chinese, Japanese, and Thai dishes. The cozy atmosphere and friendly staff make it the perfect spot for a casual meal with friends or a special night out with a loved one. Whether you're craving sushi, stir-fry, or noodles, New Asian Garden has something to satisfy your taste buds. Come and experience the flavors of Asia right here in the heart of Pittsfield.

Drifters Bar & Restaurant is a popular dining destination located at 101 Dan Fox Drive in Pittsfield, Massachusetts. This cozy establishment offers a diverse menu of delicious dishes, from savory appetizers to mouth-watering entrees and decadent desserts. Guests can enjoy their meals in a relaxed and welcoming atmosphere, perfect for a casual lunch or a special night out. With friendly staff and excellent service, Drifters Bar & Restaurant is the ideal spot to satisfy your cravings and enjoy a memorable dining experience.

Located at 635 Merrill Road in Pittsfield, Massachusetts, DICK'S Sporting Goods is your go-to destination for all things sports and outdoor gear. Whether you're in need of new workout clothes, running shoes, or equipment for your favorite sport, this store has you covered. With top brands for every season and style, you'll find everything you need to stay active and perform your best. Get ready for the holiday season with a wide selection of gifts for him, her, and kids. From golf to fishing, DICK'S has the perfect presents for every sports enthusiast. And with gifts under $50 and under $25, you can fill stockings without breaking the bank. Need your gifts in a hurry? Take advantage of free in-store and curbside pickup options for convenient shopping.

Welcome to Paula McLean Realtors Located at 54 King William Road, Lenox, Massachusetts, Paula McLean Realtors is your trusted partner in navigating the dynamic real estate market of Berkshire County. With over four decades of experience since 1981, Paula McLean has established herself as a prominent figure in the real estate industry, proudly holding four prestigious national designations: Accredited Buyers Representative, Certified Residential Specialist, Accredited Staging Professional, and Resort and Second Home Property Specialist.

Chili's Grill & Bar is a popular dining destination located at 555 Hubbard Avenue in Pittsfield, Massachusetts, United States. This lively establishment offers a diverse menu of delicious American fare, including juicy burgers, sizzling fajitas, and mouthwatering ribs. Guests can enjoy a casual dining experience in a vibrant atmosphere, complete with friendly service and a full bar serving up refreshing drinks and cocktails. Whether you're looking for a relaxing meal with friends or a fun night out, Chili's Grill & Bar is the perfect spot to satisfy your cravings.

Located at 36 Linden Street in Pittsfield, Massachusetts, The Blatt Center at Barrington Stage Company is not your typical night club. This institution is a hub for award-winning theatre in Downtown Pittsfield, celebrating its 30th Anniversary with an electrifying lineup of performances. On the Boyd-Quinson Stage, iconic shows like La Cage aux Folles, Boeing Boeing, and Next To Normal are sure to captivate audiences. Meanwhile, the St. Germain Stage offers a fresh take on classics like Romeo and Juliet with A Tender Thing, as well as thought-provoking productions like Forgiveness and Primary Trust.

Tobi's Limousine Service, Inc. is a premier transportation company located at 55 Pittsfield Road in Lenox, Massachusetts, United States. With a fleet of luxurious limousines and professional chauffeurs, we provide top-notch transportation services for weddings, proms, corporate events, airport transfers, and more. Our commitment to excellence and customer satisfaction sets us apart from the rest. Sit back, relax, and enjoy the ride with Tobi's Limousine Service, Inc.

Sportsman's Cafe Inc is a lively bar and night club located at 415 Pecks Road in Pittsfield, Massachusetts. With a welcoming atmosphere and friendly staff, this institution is a popular spot for locals and visitors alike to enjoy drinks, music, and good times. Whether you're looking to unwind after a long day or dance the night away, Sportsman's Cafe Inc has something for everyone. Come join us for a memorable night out in the heart of Pittsfield.

Redbox is a popular movie rental store located at 107 West Street in Pittsfield, Massachusetts, United States. With its iconic red kiosks, Redbox offers customers a convenient and affordable way to rent the latest movies and TV shows. Whether you're looking for a new release or a classic favorite, Redbox has a wide selection of titles to choose from. Simply visit the kiosk, browse the available options, and pick out your movie for a fun movie night at home.

The Billy Club is a charming restaurant located at 175 Lebanon Mountain Road in Pittsfield, Massachusetts. Known for its delicious food and welcoming atmosphere, The Billy Club offers a diverse menu featuring American classics with a modern twist. Whether you're in the mood for a hearty burger, a fresh salad, or a decadent dessert, The Billy Club has something for everyone. With its cozy interior and friendly staff, The Billy Club is the perfect spot for a casual meal with friends or a special night out with loved ones. Come experience the warm hospitality and mouthwatering dishes that make The Billy Club a favorite dining destination in Pittsfield.