Maryland June 21, 2023

Summer Bliss in Historic Chestertown: A Colonial Gem on the East Coast


Chestertown Farmers Market

Chestertown Farmers Market

Summer Bliss in Historic Chestertown: A Colonial Gem on the East Coast

Nestled on the East Coast, Chestertown, Maryland is a charming colonial town that exudes rich history and captivating beauty. Founded in 1706, this picturesque destination has evolved into a popular summer getaway, offering a diverse range of activities for visitors to indulge in. From boating and fishing to hiking, shopping, and cultural events, Chestertown has something to offer everyone. In this post, we’ll explore the delights of this enchanting town, highlighting its weekly farmers market, delightful accommodations, and exciting summer events that make it an ideal vacation spot.

Discover Chestertown’s Weekly Farmers Market:

One of the highlights of a summer visit to Chestertown is undoubtedly the Chestertown Farmers Market. Held every Saturday morning from 8am-12pm, this vibrant market brings together over 25 local farms, makers, and artisans, showcasing an abundance of fresh produce, artisanal crafts, and delectable treats. Stroll through the market’s colorful stalls, savor the aroma of freshly baked goods, and indulge in farm-fresh fruits and vegetables. It’s a wonderful opportunity to support local businesses while immersing yourself in the town’s warm community spirit. 

Boating, Fishing, and More:

Chestertown’s prime location on the Chester River, a tributary of the Chesapeake Bay, makes it a paradise for boating and fishing enthusiasts. Whether you’re an experienced sailor or a novice looking to embark on a nautical adventure, the town’s marina and nearby private marinas offer ample options for docking and launching. Spend your days exploring the scenic Chester River, casting a line for a bountiful catch, or simply basking in the tranquility of the water.

For those seeking outdoor thrills beyond the water, Chestertown boasts scenic walking trails that wind through town and surrounding parks. Or lace up your hiking boots and embark on an adventure to one of the area’s hiking destinations, Sassafras NRMA or Eastern Neck Island Refuge.

Charming Accommodations:

To fully immerse yourself in Chestertown’s colonial ambiance, choose from a variety of delightful accommodations. Whether you prefer the cozy charm of a bed and breakfast or the convenience of a modern Airbnb, the town offers a plethora of options to suit every taste and budget. Wake up to the aroma of freshly brewed coffee and savor a homemade breakfast before stepping out to explore all that Chestertown has to offer. 

Here are some recommendations:

Brampton Inn

White Swan Tavern

Waterfront Vacation Rental

Exciting Summer Events:

Chestertown truly comes alive during the summer months, hosting a multitude of events that showcase its vibrant culture and heritage. One of the highlights is the National Music Festival, where talented musicians from across the country gather to perform captivating classical concerts, chamber music, and more. It’s a treat for music aficionados and a testament to Chestertown’s dedication to the arts. Chestertown’s full event calendar can be found here.


Lady of the Park - Chestertown Maryland

Fountain Park, Chestertown

Visit Chestertown

Chestertown, with its rich colonial history, scenic beauty, and vibrant community, is a hidden gem on the East Coast. Whether you’re drawn to the allure of boating and fishing, the charm of a historic town, or the joy of immersing yourself in cultural events, Chestertown has it all. Explore the weekly farmers market, indulge in outdoor adventures, and partake in the exciting summer events that bring this town to life. Plan your visit to Chestertown this summer, and prepare for an unforgettable vacation filled with cherished experiences and lifelong memories.

Interested in properties in Chestertown and the surrounding area? 

Contact Peter Heller – Coldwell Banker Chesapeake