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
Quality Inn
16 Cheshire Road
Pittsfield, Massachusetts
Crowne Plaza Pittsfield-Berkshires
1 West St
Pittsfield, Massachusetts
Comfort Inn Pittsfield
1055 South St
Pittsfield, Massachusetts
White Horse Inn
378 South St
Pittsfield, Massachusetts
Berkshire Inn
150 W Housatonic St
Pittsfield, Massachusetts
BEST WESTERN BERKSHIRE HILLS
1350 West Housatonic Street
Pittsfield, Massachusetts
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St
Pittsfield, Massachusetts
Hotel Tips
Bring an actual credit card to avoid deposits and pre-authorizations consuming money in your checking account which will reduce your available balance. Hotels that accept paper cash often ask for a hefty deposit to cover potential damages in your room leaving you scrambling to find an ATM.
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.
Always announce during booking if the trip is for a special event, anniversary or reunion. Group rates can be pre-negotiated and you may qualify for a lower cost and better upgrades for your stay. If you are the one setting up the event, always work directly with the front desk manager to make sure the best service is offered to your party.
Things To Do
Pittsfield has several options for shopping for specialty food items that are not found in regular grocery stores. Shops tailored for "foodies" offer tastings of the products as well as scheduled culinary classes to perfect your skills. Shop for infused oils, salts and spices from around the World!
Pittsfield is the place to plan your wedding. You'll be spending a lot of time downtown as there are so many wonderful shops to find invitations, photographers, bakers, caterers and jewelers. Planning your wedding will be a breeze with so much support from local merchants to make a perfect and memorable day.
Pittsfield helps you expand your skills and learn some new ways to expand your artisan flare? Sign up for classes at your kitchen supply store, yarn shop, art and craft shop and photo gallery. You'll be having great fun with your new friends as you you take on that next project.
Why Do You Love Downtown?
Devany
I love downtown because there is so much life all around. From the shoppers walking the streets to the workers stocking the stores. Everybody comes together in one place, different purposes, yet all the same. Downtown stores are always so beautiful. You can see the care workers put into making their store not only clean and beautiful, but also safe and homey.
Tracy Hart
Just purchased a home nearby and am looking forward to shopping in the area
Schuyler Judd
Interesting people and shops!
Tim Dygert
Very cool stores.
Christy Richards
Because I love to shop local and the stores and owners make your visit welcoming inviting you to return again with a smile on their face.
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The American Cancer Society does not endorse any product or service.

