Downtown Pittsfield, Illinois

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

William Watson Hotel

105 E Washington St

Pittsfield, Illinois

Knights Inn Pittsfield

1238 W Washington St

Pittsfield, Illinois

Hotel Tips

Always tip staff when you feel the service was great and don't forget the housekeeping staff which you may never see. You should tip every day if you are staying multiple days as the staff may rotate out and miss the bounty at the end.

Upon check-in, slip the desk agent a tip and ask for the best room they can find at your current booked rate. Often times a quick $10 or $20 bill can go a long way towards the mood of the person who directly decides where you lay your head for the night.

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 is a great place to rent a bike and take it for a ride around downtown. There are many bike shops that sell bike and accessories as well as provide service and tuning on your ride. Don't forget your helmet and other protective gear such as reflective gear, headlight and horn.

Pittsfield brings the farming community under one marketplace to offer an assortment of locally grown fruit and vegetables. Traditionally, markets are restricted to anything grown so you can expect to see natural whole foods that are sure to please those working on their plant-based diets!

Pittsfield has so many great reasons to shop downtown as local merchants have come together to offer a wide selection of artisan gifts and foods that you are sure to find something for everyone on your shopping list of gifts. Shopping options are plentiful and all inventory is hand selected by the shop owner and then yourself so you are sure to find something special that has your style and likes in mind.

Why Do You Love Downtown?

Liisa Shunn

We love going downtown, because we like to support our local economy. The shops and restaurants we visit -- we have gotten to know the owners, so when our money is spent downtown, we know who benefits. Also? We live only a mile from downtown, so we walk or ride our bikes. No worries about a designated driver or looking for parking. We chose to live in Medford, so of course we want our money to stay in Medford, not going off to some corporate office of a chain store.

Crstal Howley

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

kristin Cutler

It's so cute and quaint.

Tammy Benson

Shopping eating and site seing

Susan Sunday

Adorable - been 1x and going back tomorrow with my friends

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