Tall ships, gathered for Downrigging Weekend in the port at Chestertown, conjure a bygone era.
Tree-lined High Street presents a colorful autumn tableau. © Michael Ventura
A schooner bears the 13-star Yacht Ensign intended for boats in inland waters. © Michael Ventura
Pedestrians congregate for the First Friday festivities, when shops, galleries and restaurants open their doors.
 The Imperial Hotel welcomes visitors. © Michael Ventura
The River Packet docks at sunset. © Stephanie Somers
Evergrain Bread Company enjoys a robust business on weekends. © Tim Fields
Carla Massoni Gallery showcases works by notable artists.
Chestertown Farmers’ & Artisans’ Market is a feast for the eyes. © Nancy McTear
 The collaborative gallery Create beckons browsers. © Jeff Weber
 The Brampton Inn is a secluded retreat of private cottages. © Jumping Rocks Photography
A cozy, cheerful bedroom welcomes guests. © Jumping Rocks Photography
A schooner bears the 13-star Yacht Ensign intended for boats in inland waters. © Michael Ventura
Pedestrians congregate for the First Friday festivities, when shops, galleries and restaurants open their doors.
 The Imperial Hotel welcomes visitors. © Michael Ventura
The River Packet docks at sunset. © Stephanie Somers
Evergrain Bread Company enjoys a robust business on weekends. © Tim Fields
Carla Massoni Gallery showcases works by notable artists.
Chestertown Farmers’ & Artisans’ Market is a feast for the eyes. © Nancy McTear
 The collaborative gallery Create beckons browsers. © Jeff Weber
 The Brampton Inn is a secluded retreat of private cottages. © Jumping Rocks Photography
A cozy, cheerful bedroom welcomes guests. © Jumping Rocks Photography

Time Traveling in Chestertown

Eclectic galleries, scrumptious edibles and dreamy boat rides enhance this historic waterfront town

Strolling the streets of Chestertown is a little like traveling back in time. A visitor might be in the midst of ordering a cranberry-orange scone with her latte when suddenly the tall ship Sultana glides into port from the peaceful Chester River, conjuring a long-ago vista. The seat of local government since 1706, Chestertown—also known as “America’s best-preserved Colonial seaport”—embraces history and the passage of time in all its rich complexity.

In fact, the Sultana—a replica of a British Royal Navy vessel that enforced those nasty tea taxes during revolutionary times—helped launch this small town into the 21st century. Since the ship’s construction was completed in 2001, educators and tourists alike have flocked to Chestertown to sail on the “Schoolship of the Chesapeake,” learn about the bay’s marine treasures and relive its history. The Sultana is also a centerpiece for the town’s many festivals. If this ship or other vessels are in port when you go, a sail on one of them will show you the town and its environs from the water. Many rural views from this Chesapeake tributary are virtually unchanged since the 1800s, and it’s great fun to peek into the backyards of the lovely waterfront homes. The Chester River Packet Company (chesterriverpacketco.com) also offers day and evening cruises on a 1920s-style tour boat.

Historic Highlights  History buffs won’t want to miss a 30-minute audio tour of the town’s waterfront area researched by scholars, performed by students from local Washington College and available via headphones at the 1746 Custom House. The self-guided tour features riveting personal stories of soldiers, slaves and revolutionaries—including Thomas Ringgold, a wealthy slave trader and “Son of Liberty” whose house is one of the stops.

A leisurely amble through town will also yield architectural and horticultural delights. Pick up a walking-tour map that will guide you past 24 mostly Colonial gems in mint condition, from the red-brick Geddes-Piper House (home of the Kent County Historical Society and its exhibits) to the 1733 White Swan Tavern, which may have hosted George Washington and is now a bed & breakfast. Washington College, to which George gave his name and some founding funds, abuts the town and is worth a meander for its scenic buildings and landscaping.

Festival Fun  Fall is festival season in Chestertown. Downrigging Weekend (October 28 through 30; sultanaeducation.org), features historic boats ranging from the pristine tall ship Kalmar Nyckel (a replica of a Swedish Colonial ship) to adorable wooden Beetle Cat sailboats. Many of the gorgeous crafts in the harbor are available for touring, and visitors can take a spin on tall ships including Sultana, Kalmar Nyckel, The Pride of Baltimore (a Baltimore clipper) and several oyster-dredging skipjacks. The festival also spotlights live music, nautical book talks and fireworks.

To coincide with Downrigging Weekend, the Chestertown RiverArts Studio Tour (October 22, 23, 28 and 29; chestertownriverarts.org) welcomes art lovers into more than 50 artisans’ studios across Kent and Queen Anne Counties. Pop into the Chestertown RiverArts Gallery to plan your tour while browsing each artist’s work, from paintings to jewelry to vases, on display there. For those planning a springtime visit, Chestertown reenacts its own version of the Boston Tea Party every Memorial Day weekend.

Arts Scene  But, if you’re not in town for a festival, try to make Chestertown’s First Friday event from 5 to 8 p.m. on the first Friday of each month, when shops, restaurants and galleries offer nibbles and special deals to visitors.

The elegant Carla Massoni Gallery (massoniart.com) showcases paintings, sculpture and woodcuts by highly regarded national artists; the nautical paintings of local favorite Marc Castelli and the works of contemporary realist Greg Mort can be found in the collection. Or visit Hegland Glass Studio (heglandglass.com), where husband-and-wife team Dave and Patti Hegland create kiln-formed art glass with intricate swirls of color and texture. The new, collaborative gallery, Create (createartcraftdesign.com), showcases the Heglands’ work, along with other fine crafts by a metalworker, a fine-furniture maker, a potter and a textile artist. Curated by Carla Massoni, these varied works are selected to complement each other. The artists can be commissioned to create pieces for public and private spaces.

Blue Canary Letterpress (bluecanarypress.com) features work by local and emerging artists along with unique cards, prints and custom designs by second-generation printer Jodi Bortz. And check out the studio of independent publisher Idiots’ Books (idiotsbooks.com), which offers quirky, satirical illustrated titles for adults and a line of children’s books. For musical performances and theater, visit the casual and intimate Art Deco Garfield Center for the Arts (garfieldcenter.org).

Fodder for Foodies  Whether you prefer coffee and a croissant at Evergrain Bread Company (evergrainbreadco.com) or local baked goods and produce from the Chestertown Farmers’ & Artisans’ Market (Saturday mornings, mid-March through December; chestertownfarmersmarket.net), you will not go hungry here. The bright and friendly Lemon Leaf Café (thellcafe.com) serves up everything from flannel cakes with homemade apricot syrup to an assortment of crab entrées. The White Swan Tavern (whiteswantavern.com) offers a traditional tea from 3 to 5 p.m. daily. And the newly renovated Kitchen at the Imperial (imperialchestertown.com ) boasts an all-you-can-eat brunch buffet with a fun build-your-own Bloody Mary and mimosa bar on Sundays.

To further titillate your taste buds, drop by Chester River Wine & Cheese Co. (chesterrivergourmet.com) for a glass (or bottle) of fine wine and an impressive cheese, olive or antipasto board.

Memorable Lodgings   If your idea of a holiday means stashing the car keys, central Chestertown has no shortage of options for accommodations from which you can walk everywhere you’ll want to go. The Widow’s Walk Inn B & B (widowswalkinn.com) and the John L. Stam House (jlstamhouse.com) are Victorian gems in the middle of town that offer full breakfasts and relaxing porches from which to watch the world go by. If driving appeals, the Brampton Bed and Breakfast Inn (bramptoninn.com) a mile outside town boasts private cottages and wood-burning fireplaces in many rooms. You’ll also enjoy a full breakfast, freshly baked cookies and afternoon tea.

Finally, Great Oak Manor (greatoakmd.com) in Chestertown offers a waterfront experience that is both elegant and active, with kayaks and paddleboards available onsite. At this inn, you’ll enjoy a lovely view of the bay with your full breakfast and complimentary sherry or port to punctuate your evening.

Amy Brecount White explores the nooks and waterways of the world from her base in Arlington, Virginia.