Downtown Chester, Vermont

Discover shopping, dining, and accommodation in downtown Chester.

Plan your trip in Chester using Travique: AI Powered Planner



Moving to Chester?

Order a Free Relocation Guide




We are seeking partnerships with forward-thinking city officials and business leaders to replicate
our system in their downtowns and launch cities together.

Shop Downtown Discount Card

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.

Shop

0 results

Hotels

Fullerton Inn Bed & Breakfast

40 The Common

Chester, Vermont

Rose Arbour Bed & Breakfast

55 School Street

Chester, Vermont

Hugging Bear Inn and Shoppe

244 Main Street

Chester, Vermont

Hotel Tips

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.

Elevators are notorious for being a nuisance so ask to be roomed on the top floor and as far away as possible. Most hotels book nearby rooms last so hopefully they have availability elsewhere.

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.

Things To Do

Chester has the perfect game shop for both young and old. Your friends and family will enjoy hours of entertainment with a wide selection of board games, card games and games of skill. A perfect stop for travellers with kids and those seeking a new adventure for game night.

Chester brings smiles by way of doughnuts and pastries made fresh daily for your enjoyment. Everyone has their favorite of course but having a variety of bakeries is what makes downtown so special. Fritters, scones and pies oh my!

Chester micro breweries have popped up in downtown corridors to quench the thirst of local or traveller whos is looking for a one-of-a-kind experience for suds brewed on site. If you are looking for a light beer or something randy and dark, you are sure to find a wide assortment of options to choose from.

Why Do You Love Downtown?

Mary Morales

DO NOT KNOW IT YET, NEW TO THE AREA

Stephanie Seavers

Close to work but also love all the small business owners, friendliness and just how supporting our local area makes me feel!

Kathy Burchett

I've never been and I would like to visit the downtown area, during my visit. During our last visit, we were not aware of a downtown area. Thank You!!!

Jennifer Moranda

Planning my first trip.

Shawna Moore

I like the old school charm and love supporting the local merchants!

Join our newsletter

Support Cancer Research

The American Cancer Society does not endorse any product or service.