A Family Hospitality History

Written by: Dylan Mason

Before the Waterside Inn began serving Chincoteague’s visitors, the property was home to Mason Seafood Company, a purveyor of fine, locally-sourced fish, oysters, and clams. Founded by Donna and Tommy Mason Sr. in 1977, Mason Seafood Co. served as a wholesale production facility that shipped seafood across the eastern seaboard for 10 years before the couple decided to branch out into the hospitality realm. The decision to create a boutique-style, family-owned and operated hotel came out of Donna and Tommy’s travels and their combined years of serving the island’s visitors in various capacities.

Donna’s father, Lee Savage, was the creator of the Dairy Dream, a soft-serve ice cream business that used ice cream trucks imported from Europe to bring delicious treats to people across the Eastern Shore of Virginia and Maryland. After the Dairy Dream’s initial success, Lee rebranded the business as Mister Whippy – it was later sold to new owners and still operates to this day as a mainstay in the island’s community. It was in this environment that Donna developed her business-minded skills and dedication to hospitality.

Tommy Mason’s service-minded skills come from his time operating a family gas station, his enlistment in the United States Coast Guard, and his lifetime in the aquaculture industry. After serving in the Coast Guard, Tommy embarked on a career dedicated to the cultivation of oysters and clams in Chincoteague’s surrounding waters. Aside from growing oysters and clams for human consumption, Tommy has partnered with the Virginia Institute of Marine Science on projects intended to study the various ways that filter-feeding bivalves can be used to help clean polluted waterways.

The Waterside Inn’s success as a longstanding family-owned and operated business would not be possible without the dedication of second and third generation Mason’s. Donna and Tommy’s son, Thomas Mason Jr., joined the family’s mission in hospitality after graduating from Old Dominion University. While developing the new business’s facilities operation methods and overseeing the grounds and housekeeping, Thomas Jr. met his future wife, Ruthann, while she was vacationing at the Waterside with friends from her home state of Delaware. The instant connection that Ruthann and Thomas Jr. made turned into a classic love story, with the couple traveling to visit each other as their bond grew stronger. Eventually, Ruthann moved to the island to be with Thomas Jr. and found herself within the fold of the Waterside Inn family, working guest relations at the front desk and learning the ins-and-outs of the hospitality industry.

After Ruthann and Thomas Jr. married in 1995, the third generation of the Mason family began to take shape, with their sons, Dylan and Ryan, being born in 1997 and 2000 respectively. As the Mason family grew in size, the Waterside Inn family was growing too, with many one-time guests turning into consistent patrons that chose the Waterside each time they returned to Chincoteague. Mutual cooperation across a family-owned business can be tricky to balance all the time, but the Mason family has relied on each other, and on the dedicated Waterside staff, throughout the years in order to bring the best hospitality solutions to the island’s visitors. Staying up to date on the hospitality industry’s trends and practices is of great importance to a multi-generational hotel’s success, so Donna and Ruthann have had to partner on strategies for keeping the Waterside’s offerings convenient, fresh, and competitive.

The sons and grandsons, Dylan and Ryan, were raised around the Waterside and in the waterways that surround Chincoteague. It was almost inevitable that Dylan and Ryan would choose to engage with the family business in various capacities, with Dylan working guest relations and Ryan working maintenance and aquaculture with his grandfather. Both Dylan and Ryan were avid baseball players in high school, which was a great point of pride for the family. Later, they each attended college, with Dylan graduating from James Madison University and Ryan graduating from Virginia Wesleyan University. Both third generation Mason’s now reside in Virginia Beach, but they each engage with the family business in various meaningful ways as they navigate their own lifepaths.

The multigenerational embrace of the family hospitality business has provided the Mason’s with countless opportunities to work with the local island community to uplift its businesses and inhabitants – it is fair to note some of those accomplishments. Donna has contributed historical items and stories to Museum of Chincoteague Island. Tommy Sr. nurtured young watermen and the waters surrounding the island, ensuring that the bounties of salty clams and oysters are preserved for generations to come. In recognition of their business prowess and community engagement, Donna and Tommy Sr. were awarded 2016 Business People of the Year by the Chincoteague Chamber of Commerce. Ruthann has served on the Historic Main Street Merchants Association, where she co-created the island’s annual Death By Chocolate event, and held positions in parent-teacher organizations devoted to keeping the island’s children safe and rewarded for their academic endeavors. Thomas Jr. has served as the most loyal of co-workers to his colleagues at the Waterside Inn, ensuring laughs and friendship during the hectic summer season, and as an unconditional supporter of youth sports on the island, always there to lend an ear or an arm to youngsters looking practice their baseball skills.

The Mason family’s hospitality story is one built on community, collaboration, mutual admiration of the outdoors, and a sheer determination to provide Chincoteague’s visitors, whether they be individual travelers or family vacationers, with the most positive, memorable island experience possible. It is a story that is still being written and lived daily, and we owe our successes to our patrons, our staff, the island community, and to the power of family.