Chestertown MarylandATTRACTIONS & THINGS TO DO
Listed below are the best attractions and things to do near Chestertown, Maryland.
1. MassoniArt Gallery
ACCLAIMED LOCAL ART GALLERY
MassoniArt Gallery is a well-respected gallery recognized throughout the Mid-Atlantic for more than 30 years. It showcases contemporary art from regional and national artists in an engaging downtown Chestertown space. Visitors appreciate its commitment to fostering creativity and supporting both established and emerging artists.
2. Garfield Center for the Arts at the Prince Theatre
HISTORIC PERFORMING THEATER
The Garfield Center for the Arts at the Prince Theatre is a community-focused performance venue housed in a beautifully restored historic theater. It presents a full calendar of plays, concerts, and educational events, enriching the area's cultural life. Local talent and professional artists alike find a welcoming stage here for theatrical and musical productions.
3. Historical Society of Kent County
REGIONAL HISTORY MUSEUM
The Historical Society of Kent County preserves and interprets the heritage of Kent County and its people. Its museum and research library contain artifacts, exhibits, and archives that offer a fascinating look into the region's past. The organization also hosts tours, lectures, and special events centered on local history.
4. Chestertown Arts & Entertainment District
CREATIVE DOWNTOWN DISTRICT
The Chestertown Arts & Entertainment District is a vibrant area in the heart of town that features galleries, studios, live performances, and public art. Strollers can enjoy outdoor sculpture, attend regular art walks, and discover unique local craftsmanship. The district plays a central role in Chestertown's creative economy and public events calendar.
5. Washington College
HISTORIC LIBERAL ARTS CAMPUS
Washington College, founded in 1782, is one of the oldest colleges in the United States and features a picturesque campus along the Chester River. Visitors can explore the historic Hynson-Ringgold House, beautiful gardens, and enjoy public lectures, concerts, and cultural programs. The college is intertwined with Chestertown's identity and local community life.
6. Downtown Chestertown Shops
SPECIALTY BOUTIQUES & GIFTS
Downtown Chestertown boasts over 200 specialty shops, boutiques, and gift stores lining its brick sidewalks. Shoppers can browse for antiques, unique crafts, clothing, and locally made goods. The welcoming atmosphere and historic architecture make shopping here a pleasant experience.
7. Brampton Inn Gardens
HISTORIC LANDSCAPED RETREAT
Brampton Inn Gardens encompass 35 acres of beautifully landscaped grounds, four of which are recognized by the National Register of Historic Places. The gardens feature lush plantings, walking paths, and tranquil spots ideal for relaxation. Overnight guests and visitors appreciate the peaceful setting just minutes from downtown Chestertown.
8. Chestertown Farmers' Market
LOCAL PRODUCE & CRAFTS
The Chestertown Farmers' Market is a weekly open-air market offering fresh local produce, baked goods, artisanal foods, and handcrafted items. Held in the heart of downtown, it brings together farmers, artists, and the local community. Visitors enjoy the lively atmosphere and opportunity to sample and purchase regional specialties.
9. Safe Harbor Great Oak Landing
FULL-SERVICE MARINA RESORT
Safe Harbor Great Oak Landing is a waterfront marina and resort offering docking facilities, lodging, a pool, and an on-site restaurant. Both boaters and land visitors enjoy its amenities and scenic setting along the Chesapeake Bay. It serves as a family-friendly hub for water recreation and relaxation.
10. Eastern Neck National Wildlife Refuge
WILDLIFE & NATURE SANCTUARY
Eastern Neck National Wildlife Refuge is a sprawling 2,300-acre island preserve located just south of Chestertown. The refuge provides habitat for migratory birds, trails for hiking and birdwatching, and picnic areas for visitors. Its scenic beauty and abundant wildlife make it a must-visit for nature lovers.
11. Adkins Arboretum
NATIVE PLANT GARDEN
Adkins Arboretum is a 400-acre native garden and preserve located within easy reach of Chestertown. The arboretum features miles of walking trails, a diverse collection of native plants, and educational exhibits. It is ideal for anyone interested in horticulture, conservation, or a peaceful escape into nature.
12. Betterton Beach
CHESAPEAKE BAY SWIMMING SPOT
Betterton Beach is a charming, family-friendly public beach located on the northern Chesapeake Bay just 20 minutes from Chestertown. With sandy shores, picnic facilities, and gentle shallows, it's a favorite local spot for swimming and relaxation. Visitors also enjoy picturesque views and sunsets over the bay.
13. Evergrain Bread Company
ARTISANAL BAKERY & CAFÉ
Evergrain Bread Company is beloved in Chestertown for its freshly baked breads, pastries, and sandwiches, made with locally sourced ingredients. The charming café setting invites both locals and visitors to relax with a coffee and a treat. It is a top dining destination for breakfast and lunch in town.
14. Luisa's Cucina Italiana
AUTHENTIC ITALIAN DINING
Luisa's Cucina Italiana is a popular Italian restaurant in Chestertown known for its welcoming atmosphere and classic dishes. Guests enjoy homemade pastas, wood-fired pizzas, and a variety of traditional entrees. The restaurant has become a community favorite for family gatherings and special occasions.
15. Sultana Education Foundation & Sultana Downrigging
TALL SHIP & MARITIME EVENTS
The Sultana Education Foundation offers hands-on environmental education programs aboard the replica schooner Sultana. Each fall, the foundation hosts Sultana Downrigging, one of the largest tall ship and wooden boat festivals on the East Coast. Visitors can tour historic vessels, enjoy live music, and learn about the Chesapeake Bay's maritime heritage.