There’s something timeless and joyful about spending time in Chestertown, Maryland. Nestled on the Upper Eastern Shore — exactly 90 miles from Washington, DC, Baltimore, and Philadelphia — Chestertown is a charming waterfront town that feels worlds away from the bustle of city life. With its historic streets, small-town vibe, and thriving local culture, it’s the perfect destination for a weekend escape.
Start your morning at the beloved Chestertown Farmer’s Market, held every Saturday rain or shine from 8 AM to noon. The market is the “go-to” spot for locals and visitors alike, overflowing with locally sourced produce, specialty foods, and artisan goods. Pick up flaky breakfast sandwiches or decadent slabs of cake from Happy Chicken Bakery; grab a container of Barbara’s famous soups; take home a cottage pie from McGlynn’s, hydroponic lettuce from Red Acres, or a pie from the Lapp Family — all surrounded by the greatest abundance of fresh, seasonal produce.
After the market, stroll through town and soak in the atmosphere. Wilmer Park, located along the Chester River, offers benches for watching boats drift by, a lively local bocce league, and a newly added children’s playground — a perfect place to relax. Chestertown is small enough that you can park your car and walk everywhere, making it a wonderfully walkable destination.
If you’re planning to stay overnight, check into The White Swan Tavern, right in the middle of town, where you can park and walk to everything. For a more private retreat, Brampton Inn Bed and Breakfast is just five minutes away — known for its stunning gardens, peaceful atmosphere, and unforgettable breakfasts. For a family gathering or a private affair, check out Chestertown’s luxury AirBNB - 114 High!
Don’t miss exploring Chestertown’s vibrant arts and shopping scene. Visit Massoni Art, where Carla curates extraordinary exhibitions of painting, photography, sculpture, and more. Browse the shelves at The Bookplate, a local favorite for books and gifts. Treat yourself to a fabulous new dress at Mimi’s Closet, and cap off your stroll with a house-made ice cream or a grilled cheese at Stam’s Luncheonette — a nostalgic local gem.
Finally, no trip is complete without a stop at Chester River Wine and Cheese, where you’ll find gourmet treats like an oil and vinegar bar, fresh-frozen pastas from Talluto’s in Philadelphia, imported Italian dry pastas, tinned fish, traditional pâtés, a large selection of cut-to-order cheeses, and John’s impeccably curated selection of wines.
Whether you’re here for the morning or staying the night, Chestertown delivers a perfect mix of small-town charm, delicious local flavors, and rich cultural treasures — making it one of the Eastern Shore’s most special destinations.
