24 Best & Fun Things To Do In Kent Island, MD

Planning a trip to Kent Island, Maryland, and looking to create unforgettable memories? Whether you’re a local or a visitor, this guide will showcase the best and most enjoyable things to do in Kent Island, MD ensuring you make the most of your time in this beautiful location.

Nestled in the heart of the Chesapeake Bay, Kent Island is Maryland’s largest island and serves as a gateway to the Eastern Shore. Known for its rich maritime history, stunning waterfront views, and outdoor recreational opportunities, Kent Island offers a unique blend of natural beauty and cultural heritage.

The island is also home to charming small towns like Stevensville and Chester. Visitors can explore the island’s scenic trails, such as the Cross Island Trail, Water enthusiasts have a handful of activities to explore from in the surrounding waters. With its relaxed atmosphere and breathtaking scenery, Kent Island is the perfect destination for a peaceful and rejuvenating getaway.

24 Best and Fun Things to Do in Kent Island, MD (2024)

1. Terrapin Nature Park

Begin your Kent Island exploration with a visit to Terrapin Nature Park, a nature preserve offering sandy beaches and a haven for wildlife.

Spanning 276 acres, the park boasts a variety of habitats, including tidal marshes, ponds, woodlands, and sandy beaches, and features a 3.25-mile oyster chaff walking trail. It is also home to a rich array of wildlife, including birds, reptiles, and aquatic species.

Visitors can enjoy the sandy shores of the Chesapeake Bay and stunning views of the Bay Bridge, spot various bird species and other wildlife, and explore the park’s diverse terrain.

Address: 191 Log Canoe Cir, Stevensville, MD 21666, United States.

2. Stevensville Historic District

The Stevensville Historic District is a charming collection of historic buildings known for its rich history and well-preserved architecture, it offers a glimpse into the region’s past and unique things to do in Kent Island, MD, for history buffs.

Located in downtown Stevensville, the district features significant buildings, such as the Cray House, the Old Stevensville Post Office, and the Stevensville Train Depot.

Visitors can learn about the region’s maritime heritage and cultural significance,  and easily access to the beautiful Chesapeake Bay and its recreational opportunities from the district.

Address: 325 Cleat Street, Stevensville, MD 21666, United States.

3. The Edge Arena

For sports lovers, an array of fun and thrilling things to do in Kent Island, MD, awaits at The Edge Arena, a multi-purpose indoor sports facility with a vast space for various athletic activities and events.

Founded in 2013, the arena hosts a wide range of sports, including basketball, volleyball, soccer, and indoor track. It is also suitable for various events beyond sports, such as concerts, trade shows, and conferences.

As a visitor to this arena, you can engage in a variety of sports and recreational activities, experience the thrill of live sporting events, concerts, or other performances, and spend quality time with family or friends enjoying different activities.

Address: 325 Log Canoe Cir, Stevensville, MD 21666, United States.

4. Kent Island Federation of Art

Art lovers can explore the Kent Federation of Art, a vibrant space exhibiting visual arts among other unique things to do in Kent Island, MD, for people of all ages today.

This center regularly hosts a variety of art exhibitions showcasing diverse styles and mediums and offers art classes and workshops for people of all ages and skill levels.

Visitors can explore and appreciate the diverse talents of local and regional artists, find inspiration for their artistic endeavors, or simply enjoy the beauty of the artwork, and learn about art through exhibitions, workshops, and events.

Address: 405 Main Street, Stevensville, MD 21666, United States.

5. Big Bats Cafe

Established in 1997, Big Bats Cafe is a laid-back sports bar known for its baseball-themed decor featuring numerous exciting things to do in Kent Island, MD, today.

The cafe is adorned with baseball memorabilia, creating a unique and immersive sports experience, and offers a wide range of menu options, including burgers, wings, sandwiches, and other pub fare.

What’s more, the cafe also provides ample viewing for sports enthusiasts to catch their favorite games and an outdoor patio for enjoying food and drinks in warmer weather.

Address: 216 Street Claire Pl, Stevensville, MD 21666, United States.

6. Cult Classic Brewing

One of the best and most exciting things to do in Kent Island, MD, for adults is to pay a visit to Cult Classic Brewing, a craft brewery known for its curated selection of fine beers.

The brewery offers a wide range of beers including American, British, Belgian, and German styles, as well as creative and experimental brews, a spacious taproom with a 75-foot bar, multiple TVs, and an outdoor patio for enjoying the weather.

Also, the brewery hosts live music and other events, creating a vibrant and energetic atmosphere, and serves a selection of food options, including pizza, burgers, and other pub fare.

Address: 1169 Shopping Center Road, Stevensville, MD 21666, United States.

7. Matapeake Clubhouse and Beach

Explore an array of fun and thrilling things to do in Kent Island, MD, at Matapeake Clubhouse and Beach, a serene environment with beautiful views of the Chesapeake Bay.

This destination features a sandy beach, a historic clubhouse, an outdoor amphitheater, picnic areas, wooded trails, and a dog-friendly beach.

Unwind and relax on the beach, take a swim, or simply enjoy the peaceful atmosphere, explore the trails, enjoy the scenery, and spend quality time with loved ones at the beach or picnic area.

Address: 2010 Sonny Schulz Blvd, Stevensville,  MD 21666, United States

8. Old Love Point Park

Enjoy some of the unique and family-friendly things to do in Kent Island, MD, today at Old Love Point Park.

Spanning 30.5-acre, the park features athletic fields for baseball, softball, soccer, lacrosse, basketball, and tennis courts, a children’s playground, picnic areas with pavilions, walking and biking trails, access to the Cross Island Trail, and waterfront access with a pier.

The park offers opportunities for outdoor recreation and exercise, family-friendly activities and picnicking, beautiful waterfront views, and a relaxing atmosphere.

Address:  300 Old Love Point Road, Stevensville, MD 21666, United States.

9. Love Point Vineyards and Winery

Love Point Vineyards and Winery is a waterfront winery that offers a serene setting with stunning views of the Chester River, where visitors searching for unique things to do in Kent Island, MD,  can enjoy handcrafted wines and the beauty of the Chesapeake Bay.

The winery boasts a beautiful waterfront setting with expansive views of the Chester River and produces a variety of award-winning wines crafted from carefully selected grapes.

Enjoy the pleasant weather in their outdoor seating areas, perfect for wine tasting and relaxation, sample a selection of handcrafted wines and discover new favorites, or enjoy stunning views of the Chester River and the surrounding natural beauty.

Address: 305 River Shore Lane, Stevensville, MD 21666, United States.

10. Save the Day Escape Rooms

Discover thrilling things to do in Kent Island, MD, for everyone at Save the Day Escape Rooms, an immersive escape room experience.

The escape room offers thrilling escape room experiences themed around classic novels, where participants work together to solve puzzles and escape a locked room within a set time limit.

Families and friends can enjoy thrilling and exciting adventures, work together to solve puzzles, strengthen relationships, and improve teamwork skills.

Address: 480 Main Street, Stevensville, MD 21666, United States.

Exploring other attractions in Maryland? Why not check out some fun things to do in Oxon-hill, MD, and fun things to do in Frederick, MD?

11. Chesapeake Chocolates

Chesapeake Chocolates offers a plethora of exciting things to do in Kent Island, MD, with kids today. Known for its handcrafted artisanal chocolates, it offers a delectable range of chocolates to suit every taste.

This establishment offers diverse handcrafted chocolate flavors including classic milk and dark chocolate, and adventurous combinations like sea salt caramel and lavender. These chocolates are presented in elegant packaging, making them perfect for gifting or personal indulgence.

Visitors can grab the perfect gift for any occasion with their wide selection of beautifully packaged chocolates, savor the exquisite taste, or learn about the art of chocolate making and appreciate the craft behind each piece.

Address: 202 Island Plaza Ct, Stevensville, MD 21666, United States.

12. Taste Buds Kitchen

Taste Buds Kitchen is a dynamic culinary offering a variety of cooking classes, camps, parties, and events for all ages.

This kitchen offers a diverse range of classes ranging from kid-friendly pizza-making to adult-focused gourmet cooking, and interactive learning. For adult classes, guests can bring their favorite beverages and enjoy them while cooking.

Visitors and locals looking for fun and educational things to do in Kent Island, MD, can enroll their kids for summer camp, school break camps, kids and family classes, or field trips to learn culinary skills, while adults can participate in classes and date nights, cooperate events, and private parties.

Address: 800-D Abruzzi Dr, Chester, MD 21619, United States.

13. Cascia Vineyards & Winery

Enjoy tops of the unique and romantic things to do in Kent Island, MD, at Cascia Vineyards & Winery, a waterfront winery overlooking the Chesapeake Bay.

Renowned for producing handcrafted premium red, white, and dessert wines from both vinifera and native grape varieties cultivated on their vineyard, the winery boasts stunning views of the Chesapeake Bay, creating a picturesque setting for wine tasting and relaxation.

The winery offers a beautiful space for hosting weddings, corporate events, and private gatherings. Visitors can enjoy a variety of delicious wines catering to different tastes and learn about the winemaking process.

Address: 200 Thompson Creek Road, Stevensville, MD 21666, United States.

14. Batts Neck Park

Visitors and locals exploring fun and unique things to do in Kent Island, MD, for people of all ages can explore recreational activities at Batts Neck Park.

Spanning 45 acres, the park boasts multiple fields for soccer, football, lacrosse, and baseball/softball, a multi-purpose artificial turf field, an in-line hockey rink, a dedicated play area for children, and ponds offering a serene natural setting within the park.

Visitors can enjoy various sports activities in the park, participate in local events and activities, or spend quality time with family at the playground and ponds.

Address: 415 Batts Neck Road, Stevensville,  MD 21666, United States.

15. Kent Island – Start Of South Island Trail

Nature lovers and outdoor enthusiasts can explore the Kent Island – Start Of South Island Trail, a popular recreational path that offers a scenic route for biking, walking, and running, providing access to various outdoor activities and natural beauty.

This 7-mile offers a scenic route for cyclists, pedestrians, and runners, stunning vistas of the Chesapeake Bay throughout the trail,  various landscapes like wooded areas, open fields, and residential neighborhoods, and easy access to the state park with its beach, picnic areas, and other amenities.

Enjoy biking, walking, running, or simply relaxing in a natural setting, soak in the stunning views of the Chesapeake Bay and the island’s diverse landscape, or embark on other activities like fishing, boating, or swimming at nearby locations.

Address: MD-18, Stevensville, MD 21666, United States

16. A1 Arcades And Rentals

Enjoy family-friendly things to do in Kent Island, MD, at A1 Arcades and Rentals, an entertainment center offering a wide range of classic and modern arcade machines for events and personal enjoyment.

This gaming center features classic arcade games, arcade game sales, and a diverse selection of arcade games for rent, suitable for various events like parties, corporate functions, and private gatherings.

Additionally, the center offers customization services for pinball machines, allowing customers to create unique gaming experiences.

Address: 1001 Butterworth Ct, Stevensville, MD 21666, United States.

17. Harris Crab House

Founded in 1981, Harris Crab House is a seafood restaurant famous for its fresh, locally sourced seafood and offers a casual, waterfront dining experience for visitors and locals alike.

The restaurant prides itself on serving the freshest seafood such as steamed blue crabs which is its signature dish alongside numerous other unique and delicious dishes.

Enjoy a casual and enjoyable dining experience with friends and family with stunning views of the Chesapeake Bay as part of the fun things to do near Kent Island, MD, today.

Address: 433 Kent Narrow Way N, Grasonville, MD 21638, United States.

18. Chesapeake Bay Sport Fishing

Embark on a fishing adventure with  Chesapeake Bay Sport Fishing, a chartered boat service offering fishing trips for people looking to explore thrilling things to do in Kent Island, MD.

Experienced captains and crew guide guests on fishing excursions, and offer opportunities to catch popular game fish in the Chesapeake Bay.

Visitors can enjoy the excitement of catching fish in a beautiful natural setting, and benefit from the knowledge and expertise of experienced captains.

Address: GS Dock, 337 Pier 1 Road, Stevensville,  MD 21666, United States.

19. Queenstown Premium Outlets

One of the many unique things to do near Kent Island, MD, today is to embark on a shopping spree at Queenstown Premium Outlets, an open-air shopping center.

Accessible within 20 minutes from Kent Island, the shopping center features designers and name-brand outlets for clothing, accessories, and shoes, and offers several restaurants and cafes available for visitors to relax and refuel.

Enjoy a pleasant shopping experience in an open-air setting, and discover something for everyone with a diverse selection of brands and merchandise.

Address: 441 Outlet Center Dr, Queenstown, MD 21658, United States.

20. Delmarva Balloon Rides

One of the most thrilling things to do in Kent Island, MD, is to enjoy a bird-eye view of the picturesque Delmarva Peninsula and its stunning landscapes with Delmarva Balloon Rides, a unique adventure that allows visitors to soar above the stunning landscapes, offering a truly unforgettable perspective.

The ballon ride features views of the Delmarva Peninsula, including its rivers, farmland, charming towns, and a variety of flight options, including sunrise and sunset flights, to suit your preferences.

Discover the beauty of the Delmarva Peninsula from a completely new viewpoint, and enjoy a peaceful and tranquil experience as you float effortlessly through the sky.

Address: 1137 Little Creek Road, Chester, MD 21619, United States.

21. Chesapeake Heritage & Visitors Center

Visitors can explore The Chesapeake Heritage & Visitors Center, a hub for exploring the rich history and natural beauty of the Chesapeake Bay region.

This museum showcases the history, heritage, and culture of the Chesapeake Bay region through interactive exhibits, and and serves as a gateway to the area, offering information, exhibits, and outdoor spaces for visitors.

Visitors looking fun fun and unique things to do in Kent Island, MD, can make a stop at the visitors center and obtain recommendations and tips from knowledgeable staff for planning your trip.

Address:  425 Piney Narrows Rd, Chester, MD 21619, United States.

22. Sandy Point State Park

Fun and thrilling things to do near Kent Island, MD, await people of all ages at Sandy Point State Park, a park known for its expansive sandy beach and a variety of recreational activities.

Established in 1948, the park boasts a mile-long sandy beach perfect for swimming, sunbathing, and building sandcastles, 22 launching ramps and a marina for boaters, multiple picnic areas equipped with grills and shelters, hiking and nature trails, and stunning views of the iconic Chesapeake Bay Bridge.

Spend quality time with loved ones in a beautiful outdoor setting, enjoy fun activities like swimming, boating, fishing, and crabbing, or hike the Corcoran Tract to observe wildlife and diverse ecosystems.

Address: 1100 E College Pkwy, Annapolis, MD 21409, United States.

23. Watermen’s Monument

Paying a visit to The Watermen’s Monument, a memorial monument dedicated to the brave men and women who have lost their lives while working in Maryland’s seafood industry should make your bucket list of unique things to do near Kent Island, MD.

Situated at the Kent Narrows Drawbridge base, the monument features a central bronze sculpture depicting two men in a rowboat, symbolizing the camaraderie and shared risks faced by watermen and offers stunning views of the Chesapeake Bay.

Gain a deeper understanding into the state’s maritime heritage and the vital role watermen have played in its development, and enjoy the scenic beauty of the Chesapeake Bay while paying tribute to the watermen.

Address: Grasonville, MD 21638, United States.

24. Breezin’ Thru Charters

Anglers and water enthusiasts can explore some unique things to do in Kent Island, MD, with Breezin’ Thru Charters, a fishing charter service that offers guided fishing trips for both experienced anglers and beginners.

This service features experienced captains and crew who provide expert guidance on fishing techniques and locations and offers all necessary gear, including rods, reels, bait, and tackle.

Learn fishing techniques and tips from experienced captains, experience the excitement of reeling in a catch, and enjoy a day on the water surrounded by beautiful scenery.

Address: 105 Riverview Road, Stevensville,  MD 21666, United States.

plan your visit to Kent Island, MD

Kent Island, MD,  presents numerous fun and intriguing activities and attractions to meet all interests and ages. Whether you’re looking for relaxation or adventure, Kent Island provides a perfect getaway with a small-town charm and picturesque views of the Chesapeake Bay. Safe trip.