Downtown Oakland, Maryland

Discover shopping, dining, and accommodation in downtown Oakland.

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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

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.

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.

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!

Things To Do

Oakland has so many great reasons to shop downtown as local merchants have come together to offer a wide selection of artisan gifts and foods that you are sure to find something for everyone on your shopping list of gifts. Shopping options are plentiful and all inventory is hand selected by the shop owner and then yourself so you are sure to find something special that has your style and likes in mind.

Oakland has several options for shopping for specialty food items that are not found in regular grocery stores. Shops tailored for "foodies" offer tastings of the products as well as scheduled culinary classes to perfect your skills. Shop for infused oils, salts and spices from around the World!

Oakland keeps your pets fed, groomed, clothed and entertained with a wide assortment of ts.s available online and in-store. Does your dog need a bit of training? Check with us for great referrals to dog walkers, trainers and veterinarians who can work with your pets.

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Why Do You Love Downtown?

Caren Murphy

Cute shops, great crab cakes, friendly.

Heather Anne Hopfinger

You do not have to walk far for a movie or some place great to shop or workout

Cathrine Sutton

Cute shops

Kathy Tidmarsh

will be staying in Aug. 2017 and looking forward to enjoying your town

Alison Barlow

Charming, lovely downtown. Love the antique shops!

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