5 Tips to Live it up Like a Local at Downrigging

There are signs of autumn on the Eastern Shore that tell us the seasons are unmistakably changing — the widening vees of southbound geese, the ghostly mists that form over cool morning coves, the scores of wooly bears hustling plushly across the road. On the Chester River, fall is heralded by the arrival of tall ships, sails bellied full as they head to Sultana’s annual Downrigging Weekend Tall Ship and Wooden Boat Festival. 

 

Now in its 18th year, Downrigging is a celebration of the majestic, timeless beauty of tall ships, but it has grown to encompass much more. Today, this three-day weekend event incorporates live music alongside the river cruises, and visitors are encouraged to wander away from the waterfront to explore a packed schedule of maritime-inspired events, activities, lectures and exhibits in Chestertown’s walkable historic district. So this November 1-3, set sail for the docks and brick sidewalks of Chestertown, where everyone from salty sailors to stalwart landlubbers will be living it up at Downrigging. 

 

 To the River! 

 Whether you know your mizzenmast from your mainmast, there’s plenty of waterfront action at Downrigging for everyone. Throughout the weekend, there are multiple opportunities to enjoy the crisp breezes and fall colors of the river onboard ships of all sorts. Whether you score a sail on the more spectacular ships (we’re looking at you, Kalmar Nyckel), or go for a more intimate experience onboard Lady Maryland or Sigsbee, the four cruises throughout the weekend provide a time-travel experience to the Chesapeake’s golden age of sail. Looky-loos can get in on the action, too, during the morning open houses, when the tall ships and visiting wooden boats are open to the public. Stroll along the docks for a close-up look at carved figureheads and gilded trailboards, and cross catwalks for a quick tour of wooden boats both big and small. And classic boat enthusiasts will geek out on Saturday and Sunday over the gorgeous Chris Craft eye candy at the Antique and Classic Boat Society exhibit at the foot of High Street. 

 

 

Trip the Light Fantastic 

Downrigging doesn’t stint on spectacles, and whether you’re an ardent shutterbug or a photog just doing it for the ‘Gram, you’ll find plenty of fantastic material in the weekend’s festivities. The best shots come courtesy of the Chester River Bridge, which affords a birdseye view of the waterfront packed cheek-to-jowl with dozens of schooners, skipjacks, and other iconic watercraft. The ships are illuminated during the festival each evening at 6 p.m, so prepare to post up for a prime spot on the bridge’s south-facing sidewalk — especially for the fireworks on Saturday evening that, combined with the river’s reflection and the glowing forest of rigging, are truly an unforgettable sight. 

 

Blue Grass + Wooden Boats = <3 

 If tall ships don’t float your boat, there’s plenty of other Downrigging entertainment to enjoy. Local secret — Downrigging is the best lowkey bluegrass festival on the Eastern Shore. The festival’s organizers have been steadily adding to the list of performances over the years, and 2019’s event boasts a full music village with 12 different bluegrass acts from the local favorites the High and Wides to regional acts like Caleb Stine, Betty and the Bullet, and the Dirty Grass Players. Music can be enjoyed all weekend long, with an all-access weekend pass setting you back only $20 for the early bird rate. True diehards can also stick around for a Saturday late-night bluegrass show at the historic Garfield Theater, where the Dirty Grass Players and the High and Wides will team up for an epic evening of finger pickin’ and foot stompin.’ Be sure to reserve your tickets in advance — seats to this will go fast. 

 

The Bay’s Boats, by Book and by Brush 

 Downrigging is all about boats — and that extends to events and exhibits in Chestertown proper, too. Fans of regional artist Marc Castelli should stop by Massoni Gallery on High Street to see this year’s annual exhibit, “Kings Tide,” and to rub elbows with the artist, known for his sensitive documentary watercolors exploring watermen’s work and the Chesapeake environment. On Saturday afternoon, maritime history fans have plenty of fodder. Check out a talk by author Brian Hope on his new book, “Bay Pilots — A History of Maryland Pilots Association,” hosted by cult classic bookshop, The Bookplate, at 1 p.m. Afterward, head down to Sultana Education Foundation’s Holt Center for two maritime-inspired back-to-back talks at 3 and 5 p.m. Jim Tildesley, former director of the Scottish Maritime Museum, is on first discussing his new book about the life of Admiral John Inglis (who, spoiler alert, also happened to be captain of the original Royal Navy schooner Sultana). Stick around for a talk by Chesapeake writer Tom Pelton, discussing stories from his new book, The Chesapeake in Focus. 

 

Go With the Flow 

 When attending Downrigging, keep an open mind about how ‘maritime’ can be interpreted. Chestertown enthusiastically embraces Downrigging by weaving in all sorts of spirited events that vary in their relationship to the water, creating a festive and motley atmosphere in keeping with the town’s eclectic vibe. On Friday night, check out the free student art exhibit at the Chestertown Marina Office. Hosted by the Kent County Arts Council and Arts-in-Motion, the mixed-media works exhibited were created by 8th grade public and private Kent County students, inspired by African-American maritime history during the Revolutionary War. The next day, runners can join a 5k or 10-mile Run for Clean Rivers to benefit ShoreRivers at 9 a.m., but make sure to keep up your pace so you don’t miss the 10 a.m. Chestertown Halloween Parade. Grab a coffee and stake out a spot on the sidewalk for a slice of Americana as nostalgic as pumpkin pie. The event runs for several blocks down the middle of High Street and concludes at the waterfront. 

 

If You Go: 

Tickets to sail on the ships and attend the bluegrass village need to be booked in advance at: http://downrigging.org. The event will continue rain or shine, but sails may be affected by strong storms or dangerous inclement weather, so follow Sultana Education Foundation on Facebook for updates, or sign up for their e-news. 

 

The full event schedule is also online at: http://downrigging.org. Attendees should be prepared for some walking, as Chestertown’s downtown area encompasses the waterfront and several blocks of storefronts, parks and homes.

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