From Bethesda Magazine: Best of Chestertown

This art-forward town on the Chester River offers historic strolls, a sculpture trail and yummy local bites

July 16, 2026 9:09 a.m.

Chestertown on the Chester River Port. Photo Courtesy Sultana/ by Chris Cerino

This is the fourth part of The Best of The Bay July/August cover story for Bethesda Magazine. St. Michaels was published Monday, Cambridge was published Tuesday and Easton was published Wednesday. Feature on Tilghman Island will be published in the coming days.

Harkening back to 1706, Chestertown on the Chester River is one of America’s best preserved Colonial ports, with many Federal, Queen Anne and Victorian structures still intact. This small college town (the population is less than 6,000) is walkable, with High Street as its main drag. Visitors can enjoy the pedestrian- and bike-friendly trails and opportunities to get river-top views from kayaks and boats. Artisans of glass, grains and canvas have found this a welcome spot to set up shop. The town buzzes on its many festival weekends, including a tea party reenactment (according to local legend, Chestertown re-created the Boston Tea Party after hearing that Boston Harbor had been closed), a downrigging weekend with tall ship cruises, and a “Dickens of a Christmas” holiday celebration.

Best Tours of the Town

Take the town’s self-guided walking tours separately or simultaneously. The eclectic Peter and Hanna Woicke Collection boasts 23 modern outdoor sculptures to admire and ponder. Finding each can be like a scavenger hunt for all ages to relish. (The map is online and at local businesses.) Pick up the Historical Society of Kent County’s self-guided, 29-stop tour outside the  Bordley History Center to dive into Colonial, African American and more recent local history. If you schedule two weeks out, the society offers guided history tours and ghost walks for groups ($20 per person). It also offers tours on festival weekends.

Peter and Hanna Woicke Collection, chestertownpublicarts.com

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Bordley History Center, 301 High St., 410-778-3499, kentcountyhistory.org

Best Overnight Elegance

Brampton 1860, a stately brick manor built in, yes, 1860, also offers cottages (two are dog-friendly) and 35 acres of gardens and meadows to stroll through, not far from town. A stay includes a full gourmet breakfast and afternoon tea with freshly made sweet and savory treats. Great Oak Manor features 15 acres to explore with a private beach where Fairlee Creek meets the Chesapeake. Its farm-to-table breakfasts and lunches are open to guests, and gourmet dinners now welcome the public. On special weekends, top chefs from around the country offer immersive cooking demos, talks and intimate meals. In town, check out the recently refurbished White Swan Tavern.

Brampton 1860, 25227 Chestertown Road, 410-778-1860, bramptoninn.com

Great Oak Manor, 10568 Cliff Road, 410-778-5943, greatoakmanor.com

Best Arts to Admire (and Shop)

At the stunning Hegland Glass gallery, ooh and aah at the carefully crafted and colorful bowls, platters and other pieces of kiln-formed, award-winning glass art. The husband-and-wife team of Dave and Patti Hegland is often on hand to answer questions, and they offer intimate two-day classes to help you create a glass masterpiece. Nearby, the Chestertown RiverArts gallery showcases pieces from local potters, painters and jewelry designers. RiverArts also sponsors regular classes and art-focused events to spotlight the vibrant talents hereabouts, including First Friday Opening receptions (all year) and seasonal open studios.

Hegland Glass, 315 High St., 410-870-5432, heglandglass.com

Chestertown RiverArts, 343 High St., 410-778-6300, ctownra.org/events

Best Bites

Head to the cozy Evergrain Bread Co. for your morning jolt with a brown sugar latte or a Nutella hot chocolate. Its rotating offerings of freshly baked goods might include mouthwatering apricot ginger scones, fresh baguettes or a pistachio brioche. A newer kid on the block, Modern Stone Age focuses on traditional culinary methods and is known for its wild sourdough fermentation, local ingredients and practicing the nose-to-tail whole use of animals. Bill Schindler co-owns the restaurant/bakery with his wife, Christina, and is an associate professor at Chestertown’s Washington College and author of Eat Like a Human. Check out the Friday night pizzas (red, white and meat lover) with fermented french fries.

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Evergrain Bread Co., 201 High St., 410-778-3333, evergrainbreadco.com

Modern Stone Age, 236 Cannon St., 410-996-4776, modernstoneage.com

Christina and Bill Schindler. Photo by Stephanie Stomers.

Best Gallery

Art enthusiasts should check out Carla Massoni’s gallery, MassoniArt, which presents many accomplished mid-Atlantic artists, along with D.C.-area talents. An arts proponent for more than 35 years, Massoni changes her gallery exhibitions often and features award-winning landscape artists, printmakers and sculptors. A local favorite and frequent exhibitor, Marc Castelli’s Eastern Shore-focused painting subjects include log canoes (which are raced locally), Chesapeake area workboats and images from past downrigging weekends.

MassoniArt, 113 S. Cross St., 410-708-4512, massoniart.com

Best River Adventures

While riverside, check out the impressive Sultana, a reproduction of a 1768 British schooner, that resides here. Focusing on Colonial history and environmental education, the nonprofit Sultana Educational Foundation offers two-hour, hands-on sails aboard the tall ship on select weekends through the summer and into fall ($40; $20 for ages 5-12). To learn about local ecosystems, take the foundation’s 2½-hour guided kayak tours along the river and its tributaries through the summer and into fall ($45 for age 12 and older only). The Chester River Packet Co. offers two-hour themed cruises aboard a 1920s-style tour boat from April through November that include a “casual cuisine” evening meal or Sunday brunch ($50; $25 for ages 4-10) and shorter guided tours on Saturday afternoons.

Sultana, Chestertown Marina, 207 S. Water St., 410-778-5954, sultanaeducation.org

Chester River Packet Co., High Street Town Dock, 410-625-0312, chesterriverpacketco.com/public-cruises

This appears in the July/August 2026 issue of Bethesda Magazine.

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Originally published at Bethesdamagazine