Downtown Chester, New York

Discover shopping, dining, and accommodation in downtown Chester.

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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

Holiday Inn Express Hotel & Suites Chester

2 Bryle Place

Chester, New York

GLENMERE MANSION

634 Pine Hill Road

Chester, New York

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.

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.

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

Chester visitors are always welcome and you will receive exceptional service from local merchant-owners as opposed to staff at the big box retailers. We take the extra time to make sure that you how to make best use of your purchase and that you get exactly what you need.

Chester gives several options to find the right piece of art as it takes time and a diligent effort to get just the right piece. Shopping for art downtown is the best way to locate your next purchase.

Chester 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.

Why Do You Love Downtown?

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!

Channal Styers

Will be my first visit taking Easter train ride on Saturday to Watertown super excited see what in this great town!

Dorothy Wilson

Unique shopping-love the atmosphere

Deborah Berg

It's beautiful.

Rebekah Nelson

I'm visiting for the first time next week and I'm considering relocating to Ashland. I've heard so many great things about it!

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