Downtown Oakland, Tennessee

Discover shopping, dining, and accommodation in downtown Oakland.

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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

Oakland Inn

6808 Hwy 64

Oakland, Tennessee

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.

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.

Always find a reason to email the front desk manager in hotels that you plan to visit again. Tell them what they did right and express your plans to stay again and ask what opportunities there might be for frequent discounts or upgrades on your next visits. If you become friends with the manager, you just might get the friends and family rate some day.

Things To Do

Oakland brings a custom fit every time a shoe is bought locally. Nothing beats the hands on experience of shoe shopping to add to your collection of Men's, Women's and Children's shoes. Try them on, walk around and make sure you have the best fit as every manufacturer is a bit different on sizing.

Oakland 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.

Oakland has that special dining venue and you are sure to find something to please with numerous meals served to satisfy each palette. A wide variety of restaurants and delis are available to choose from with a nice selection of entrees and especially desserts.

Why Do You Love Downtown?

Tracy Hart

Just purchased a home nearby and am looking forward to shopping in the area

Robert Drennan

Planning a trip and want to visit after reading all the reviews

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!

Jackie Avery

I love supporting locals, the view, and atmosphere!

Snow Charpentier

It's grown and changed so much since I moved away for a few years and came back. Great to see a lot of smaller businesses expanding and hoping to contribute to the growth of downtown Medford.

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