Downtown Winchester, Kentucky









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.









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Things to do in Winchester, Kentucky

Main Street of old Downtown Winchester speaks to once what was and what could be once again. As Winchester 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 Winchester thanks the collection of small business owners who devote their time and energy to make shopping downtown a great experience. Inventory offered downtown is shopped by the merchant buyer to bring the best products to your neighborhood.

Downtown Winchester 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.

Downtown Winchester can warm you up on a cloudy day or simply offer your daily perk by visiting your local coffee shop. Quality, purity and punch are targeted with coffee beans curated globally and locally roasted while being served fresh as it is made right in front of you. Order up!

Downtown Winchester has a great collection of barber shops to choose from if you want to take a little off the top, get a clean shave or to trim your moustache or beard. Take a moment to consider buying some styling gel, beard oil or wax and always tip well.

Why do you love downtown?

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!!!

Darby
Visiting in July for the 1st time!

Sophie Jacobson
I love downtown because it offers something for everyone!

Alison Barlow
Charming, lovely downtown. Love the antique shops!

Bob Puthoff
I'm sending some clients there this Summer and want to get them a discount card to shop. Thanks!

Restaurants in Winchester, Kentucky


Big Daddy Sals Restaurant

1131 Mcclure Road
Downtown Winchester



Ancestors Soup

553 Country Club Court
Downtown Winchester



Bartons Restaurant

516 Boone Avenue
Downtown Winchester



2 Mamas Cookin For You

134 Fontaine Boulevard
Downtown Winchester




Downtown Winchester Hotels

Finding the best hotel in Downtown Winchester 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:

Not all online booking systems are fully integrated with hotel reservations systems so there is a chance that smaller hotels are hand entering your stay from a fax machine which leaves room for errors. Book directly with hotel to avoid any problems and ask for a price match if you find a better price online.

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.

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!