Need a charming Eastern Shore getaway with colonial history, riverfront views, and small-town charm? Head to Chestertown! Nestled along the Chester River in Kent County, Chestertown is one of Maryland’s best-preserved historic towns. With cobblestone streets, Georgian architecture, and vibrant cultural life, this walkable riverside town blends history, nature, and modern creativity for a delightful escape.
Chestertown, MD Highlights:
- For Adventurous Travelers: Kayak or paddle the Chester River – Rent a kayak or launch from Wilmer Park to explore the peaceful waterways and scenic shorelines.
- For History Buffs: Stroll the Chestertown Historic District – Admire 18th-century brick homes, churches, and the colonial-era Customs House on a self-guided walking tour.
- For Shoppers: Browse High Street boutiques and galleries – Discover antiques, books, art, and gifts in locally owned shops with Chesapeake charm.
- For Couples: Enjoy a wine tasting or romantic stay at a historic inn – Share a sunset drink riverside or relax in a cozy B&B with centuries-old charm.
- For Families: Explore the Sultana Education Foundation or attend a community event – Learn about Chesapeake Bay ecology aboard a replica 1768 schooner or enjoy free concerts in the park.
Best Time to Visit Chestertown, MD
The best time to visit Chestertown is spring through fall (April–October), when the weather is mild and perfect for waterfront walks, festivals, and outdoor dining. Fall brings foliage and harvest markets, while spring offers garden tours and sailing events.
How to Get to Chestertown, MD
- If you are traveling by car: Chestertown is located off MD-213, about 1.5 hours from Baltimore, Philadelphia, or Washington, D.C.
- By Air: The nearest airports are Baltimore/Washington International (BWI) and Philadelphia International (PHL), both within 90 minutes by car.
- By Bus: Limited regional services are available; driving remains the best option for flexibility and exploring nearby small towns.
Where to Stay in Chestertown, MD
- The White Swan Tavern – Historic 18th-century inn offering elegant rooms and full breakfast in a colonial setting.
- Great Oak Manor – Waterfront B&B on the Chesapeake Bay with stunning views, cozy fireplaces, and expansive grounds.
- The Inn at Huntingfield Creek (nearby Rock Hall) – Peaceful countryside retreat with suites and cottages, perfect for couples and nature lovers.
Best Things to Do in Chestertown, MD
More Places to Eat in Chestertown, MD
- Blue Heron Café – Cozy spot for breakfast, lunch, and baked goods with seasonal menus and friendly service.
- The Kitchen at the Imperial – Upscale American fare served in a historic downtown hotel with charming ambiance.
- 98 Cannon Riverfront Grille – Elevated dining on the water offering steaks, seafood, and a relaxing riverside patio.
If you are interested in local events:
- Chestertown Tea Party Festival (May) – Revolutionary War reenactments, parades, and colonial fun commemorate a 1774 protest against British rule.
- Chestertown First Fridays – Monthly downtown celebration with gallery openings, live music, shopping, and community spirit.
- Chestertown Jazz Festival (September) – Outdoor concerts and performances featuring regional and national jazz musicians.
If you are looking for unique day trips within 30–60 Minutes of Chestertown, Maryland:
- Rock Hall (20–25 min) – Quaint Chesapeake Bay town with marinas, seafood restaurants, and sunset cruises.
- Eastern Neck National Wildlife Refuge (30 min) – Peaceful island sanctuary with birdwatching trails and bay views.
- Galena (15–20 min) – Small town with antique stores, wineries, and scenic drives along the Sassafras River.
- Betterton Beach (25 min) – Quiet Chesapeake beach town perfect for swimming, sunbathing, and picnics.
- Centreville (30 min) – Historic Eastern Shore town with charming architecture and nature parks nearby.
I get asked this a lot so I decided to include it:
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Question: Where is Chestertown located, and what is its significance?
Answer: Chestertown is the lovely county seat of Kent County, originally founded in 1706 as one of Maryland's Eastern Shore's earliest settlements and most influential port cities. -
Question: What type of architecture is preserved in Chestertown?
Answer: Chestertown features preserved colonial-era and pioneer-era architecture, with many landmarks listed on the National Register of Historic Places. -
Question: What are some notable landmarks in Chestertown?
Answer: Notable landmarks include the Chestertown Railroad Station, Airy Hill, and the buildings of Washington College. -
Question: What annual festival does Chestertown host, and what does it commemorate?
Answer: Chestertown hosts the annual Chestertown Tea Party Festival, which commemorates the 1774 event following the Boston Tea Party earlier that year.
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