Classes and tours offer visitors outstanding way to experience Dorchester!

By Amanda Fenstermaker, Director Dorchester Tourism

When Angela Thomas leads her popular “Yoga Under the Sail” or Stand-Up Paddleboard (SUP) classes at the Sailwinds Visitor Center, participants always laugh at her refrain ‘don’t worry if you lose your balance, just be sure to take your neighbor with you when you fall!’

stand up paddle board classes at the Sailwinds Visitor Center

With a thousand kilowatt smile and open-hearted style, this fitness pro creates engaging experiences on land and water. Whether repeat customer or visiting vacationer, participating in one of Angela’s classes has become a top 10 experience in the heart of the Chesapeake.

Angela PhillipsA native of Dorchester’s Elliott Island, Angela built a reputation as an exceptional fitness coach. For more than 15 years, she’s been a fixture on Dorchester’s wellness scene while working at the YMCA and Power House Gym. A Level 2 PaddleFit and yoga instructor, she’s also certified in Group fitness, Pilates, kick-boxing, Total Strength, Body Pump, and Spin.

But it was the 10’ Suplove SUP board that started her entrepreneurial journey.

“In the summer of 2012, my husband Johnny and son Seth took a SUP class with me in Ocean City. I was immediately hooked and brought four boards home,” she said. “When I couldn’t get my family to paddle with me, I started taking my girlfriends out.”

After two years leading these SUP excursions, friends and family encouraged her to channel her experience and enthusiasm into a new venture. She drew up a business plan and launched Over Board Paddle and Fitness in 2014. By 2017, business quadrupled and she expanded with new equipment and custom classes and tours.


“I love bringing people to Downtown Cambridge along the waterfront. It’s amazing for beginners because the cove – located right next to our visitor center – creates a safe and accessible space to start,” she said. “We literally tour Cambridge’s maritime history, paddling by the Choptank Lighthouse and marina into Cambridge Creek past Claytons, the old ship yard and Snapper’s Restaurant.”

stand up paddle board at Suicide Bridge restaurant

Adept at moving first-time paddlers from wobbly knees to confident stance, Over Board uses high quality, oversized paddle boards that are stable, heavy and very forgiving.

With Dorchester’s large number of vacation rentals and special event venues, Angela found that many visitors were looking for ‘custom’ activities. To help meet this demand, Over Board now offers group tours and classes for weddings, birthday parties, reunions and family vacations for groups ranging from three to 14 people. She trailers the equipment directly to visiting vacationers.

Never one to rest on her laurels, last year, Angela acquired a Big Buddha flow motion yoga pod. Designed for on-water workouts, the novel floating ‘pontoon’ is the first of its kind in Dorchester County. Each station is a cross between a paddleboard and a yoga mat. Eight mats are connected and surround a center pod where she coaches each class through a total body workout.

“The Flowmotion Fitness Pod is magic, it’s like a floating yoga/fitness studio! You get to enjoy all the elements of the water while engaging tons of stabilizer muscles and firing your core to a whole new level.”

The yogi recently teamed up with her friend, fellow entrepreneur Kelly Testerman-Jackson – owner of Emily’s Produce – to present “Goat Yoga.” While this newest practice has become a YouTube sensation and is popular from Portland, Maine to Portland Oregon, the duo’s goat yoga were the first such special events held in Dorchester County. The sessions have helped drive interest and awareness of both businesses according to Testerman-Jackson.

“Our family business values the partnerships that we have with our customers and especially those we have with like-minded businesses who care about the health and wellness of our community. Supporting local agriculture comes in a variety of ways, and our unique partnership with Angela proves that for sure!”

On Friday evenings during warm weather, Angela can be found leading “Sunset SUP” at Suicide Bridge Restaurant in East New Market. The events have become a favorite ‘happy hour.’ Post-SUP, the paddlers are treated to a complimentary cocktail. After an engaging 60-minute tour, many stay for dinner or drinks with friends or fellow paddlers.

To see a complete schedule of yoga and SUP classes, or to book a private event, contact Angela by email or phone (410) 463-4350 or visit her website. Special thanks to local photographers Bill Whaley and Jameson Harrington for providing photos of Over Board in motion.

Overboard Paddle and Fitness operates seven days a week beginning at 8 am. Outdoor classes and tours at the Sailwinds Visitors Center and Suicide Bridge Restaurant are weather dependent. Advance registration is encouraged. Private tours and classes available.

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