Downtown Pittsfield, Massachusetts
Discover shopping, dining, and accommodation in downtown Pittsfield.
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ShopDowntown.org Discount Card Program
The ShopDowntown.org Discount Card Program encourages local shopping by offering exclusive savings at participating downtown businesses. Shoppers can obtain a discount card by donating $20 or more to the American Cancer Society, unlocking deals of up to 15% off at local stores. The program supports small businesses, funds community health initiatives, and helps strengthen the local economy, making it a win-win for both merchants and consumers.
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Hotels
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St
Pittsfield, Massachusetts
Berkshire Inn
150 W Housatonic St
Pittsfield, Massachusetts
White Horse Inn
378 South St
Pittsfield, Massachusetts
BEST WESTERN BERKSHIRE HILLS
1350 West Housatonic Street
Pittsfield, Massachusetts
Comfort Inn Pittsfield
1055 South St
Pittsfield, Massachusetts
Quality Inn
16 Cheshire Road
Pittsfield, Massachusetts
Crowne Plaza Pittsfield-Berkshires
1 West St
Pittsfield, Massachusetts
Hotel Tips
Not all online booking systems are fully integrated with hotel reservations systems so there is a chance that smaller hotels are hand entering your stay from a fax machine which leaves room for errors. Book directly with hotel to avoid any problems and ask for a price match if you find a better price online.
Avoid booking poolside for kids playing during the day and gatherings at night. Sound bounces off of the water and voices carry so ask for a room away from the pool either on the opposite side of the hotel or in higher floors.
Most hotel offer a complimentary breakfast bar or even a full cafe meal with your choice of a full menu. Keep in mind that some offer nothing at all so it is a good idea to pack a few packets of instant oatmeal for a quick and easy meal before you head out for the day.
Things To Do
Pittsfield hosts several events per year for your listening enjoyment but visit your piano shop to learn how to play and possibly purchase your grand, upright or digital piano. Don't forget the specialty work involved such as tuning and moving which are performed by skilled technicians.
Pittsfield brings musicians together and finding your local musical instrument shop can be a great way to get to try new and used guitars. Be sure to start your search downtown if you are looking to upgrade, trade-in or add to your collection.
Pittsfield keeps your pets fed, groomed, clothed and entertained with a wide assortment of ts.s available online and in-store. Does your dog need a bit of training? Check with us for great referrals to dog walkers, trainers and veterinarians who can work with your pets.
Why Do You Love Downtown?
Snow Charpentier
It's grown and changed so much since I moved away for a few years and came back. Great to see a lot of smaller businesses expanding and hoping to contribute to the growth of downtown Medford.
Deborah
Jacksonville is utterly charming! I love browsing Terra Firma and Pickety Place, eating delicious Umi Sushi, and sitting under the amazing wisteria in the Bella Union garden. I always go to the library in that sweet little building, where Lauren the librarian knows me by name (and recommends good books). The Good Bean people are awfully nice, and even the clerks at Umpqua Bank are especially kind and friendly. Best little downtown ever!
Darcie Maassen
I love Downtown because I love the beautiful historic buildings. It's a very pretty area aesthetically. I also appreciate the great variety of delicious dining within a small area. Favorites include Capers, Pomodori, Paisanos, Bricktowne Brewery, Elements Tapas bar, Porters, Larks and 4 Daughters. They are all within 4-5 blocks!
Susan Sunday
Adorable - been 1x and going back tomorrow with my friends
Megan H.
I love being able to browse a variety of my favorite restaurants and bars, all within easy walking distance of convenient parking. Enjoying local fare and live music downtown after a grilling day at the office makes every day feel like the weekend.
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