Downtown Bennington, Vermont









About Us


Shop Downtown Discount Card

Discounts For Customers - Support Local Businesses - Fight Cancer

When you purchase a Shop Downtown Discount Card for $10, you help support your neighbors, local economy and the American Cancer Society's mission to save lives, celebrate lives and lead the fight for a world without cancer. You also ensure great savings on a variety of products and services every time you patronize a participating member. It's a win/win situation.

Shop Downtown will contribute 100% of the sale price of each discount card sold through December 31, 2021, to American Cancer Society Relay For Life. The American Cancer Society does not endorse any product or service.









Downtown Merchants
Sign up for free!






Things to do in Bennington, Vermont

Main Street of old Downtown Bennington speaks to once what was and what could be once again. As Bennington the community gathers, it leaves a pocket of opportunity for small business owners to come in and set up shop.Take a few minutes to explore what each downtown has to offer by viewing our directory below.

Downtown Bennington 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.

Downtown Bennington shopping is better than online shopping so that you can touch, feel, smell and taste as an experience with an item before deciding to purchase it for yourself or as a gift. Local merchants have hand selected their inventory to provide a unique selection for your downtown.

Downtown Bennington 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.

Downtown Bennington 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?

Angela Shields
I will be visiting Ashland for the first time this coming weekend! I have heard from numerous people what a great town it is and how much I will like it. Very excited to check it out and do some shopping!

Jeremy Holmes
Supporting small business downtown is a very real way to support your local community. Downtown businesses are locals, like us.

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

Kim Ward
Unique and wonderful shopping.

Manuel Del Jesus RamosVasconcelos
Nice Beat

Restaurants in Bennington, Vermont


Bennington Station Restaurant

150 Depot St
Downtown Bennington




Downtown Bennington Hotels

Finding the best hotel in Downtown Bennington can make or break the experience of your entire trip. Take a few minutes to explore what each hotel has to offer by viewing our directory below. Here are some tips to consider:

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.

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.