Wine, Walking & Waterfront

Jan Downs photography

There’s no denying the immediate appeal of St. Michaels. Whether you approach by land or on the water, the town’s lovely harbor, historic buildings and inviting shops just ooze Chesapeake charm. There’s no bad time to visit, but this town that really knows how to party, with multiple festivals throughout the year that transform the community into a Christmas wonderland, a hub for runners, and of course, a wine-drenched bacchanalia.

The Winefest at St. Michaels, set for April 28 and 29 this year, brings in more than 14 wineries and wine distributers, spreading them across the downtown area, with pouring stations set up in gardens, inside boutiques, and right on the sidewalks. A relaxed stroll down leafy streets becomes a treasure hunt full of generous pours.

This writer was lucky enough to be invited to the 2017 Winefest for a girlfriends’ getaway, and the weekend did not disappoint. The unseasonably warm April weather made it feel like the quintessential St. Mike’s summer destination weekend. Stemless tasting glasses in hand, we worked our way up Talbot Street and back again—sipping responsibly, of course. With tasting destinations all over town and no set schedule, we also took some detours through some of the town’s art galleries and boutiques. After a leisurely lunch to refuel and hydrate, we caught our second wind and jumped back into the mix, ready for the next round of whites, reds and rosés.

Local organizers believe that Winefest, now in its ninth year, is the only streetscape wine festival of its kind. It also marks the beginning of the tourist season for the Main Street shopping district, when blue skies and balmy temperatures attract thousands of visitors. Hotels and B&Bs throughout Talbot County and Cambridge sell out, and Winefest co-founder John Marrah says the festival brings in the most revenue of any event in town all year.

“Those retailers who cater to the wine tasting clientele have reported some of the busiest days of their year during Winefest,” he reports.

Marrah is the owner of St. Michaels Tourism and Patriot Cruises, which operates a replica 1930s steamboat. Patriot hosts special VIP tastings of high-end wines during the festival with the St. Michaels harbor as its stunning backdrop.

The festival’s proximity to the waterfront adds another unique element: Instead of just dock and dine, boaters can dock and sample wine. Some Winefest attendees come by boat, and Marrah says it’s the first weekend of the year when the marinas fill up.

During my Winefest weekend, I ran into Jen Dadamo and Brianna Creed, who had come from Annapolis by boat as a fun girls’ getaway. They sailed over on a 40-foot Irwin, Sea Cooper, and stayed overnight at St. Michaels Marina.

“We loved all the wines, wonderful boutiques and the beautiful historic town,” said Dadamo and Creed.

For WineFest boaters who’d rather let someone else do the work of crossing the Bay, Watermark Cruises offers a package to take you from Annapolis to St. Michaels by boat for the festival, enjoy the day, and then cruise back to Annapolis.

However you choose to arrive, Marrah advises people who want to go this year to buy tickets early. VIP always sells out, he says, and this year, regular tasting tickets will also be limited because of the festival’s growing popularity. 

Meg Walburn Viviano is CBM’s Bay Bulletin news director. Subscribe for free at