Downtown Pittsfield, Massachusetts

Hotels

Hotel Tips

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.

Other sources of noise can be opening and closing trash dumpsters and also during collection by garbage trucks. Another great question is if they have any renovation plans, or underway that could affect your ability to relax. Pack earplugs and eyeshades!

Policies vary on the availability of pet friendly rooms to it is wise to be open, honest and upfront during the booking process. You may find yourself kicked out or even paying a large deposit if you are not in a pet-friendly hotel and bring one anyway. New ADA laws are fuzzy though as service animals are not required to be documented and proprietors are legally not allowed to ask if the animal is a pet vs. a service animal.

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 offers on-the-go dining when you visit your favorite food truck. Pick up some corn tortilla tacos with freshly made pico with a fresh squeeze of lemon to give your day a boost. Food trucks can offer a wide variety of niche ethnic blends.

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?

CJ
Great vibe to this town! My mom lives in Medford so when I come to visit, I like to stop in Ashland.

Deborah Berg
It's beautiful.

Crstal Howley
Hoping to enjoy your downtown. This is my first trip!!!

Sharon Wright
I like the idea of downtown merchants being more visible and that they are locally owned and operated. It's great to see what's available downtown and I look forward to the discounts as well. Being a history buff, I love see the architecture as it was back in the day which is lost in modern buildings. Downtown is charming, inviting and quaint!

Judy Dechent
My daughter and her fiance are relocating from PA to Ashland. They leave next week. I've heard nothing but great things from them and look forward to visiting.

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