26 Best & Fun Things to Do in Kent Island (MD)

Kent Island is situated in the state of Maryland and is said to be the largest Island in the Chesapeake Bay. The first settlers in Kent Island were Native Americans who lived there for almost twelve thousand years.

Kent Island recorded a population of more than sixteen thousand after the 2000 census in the United States.

The Metapeake tribe later settled in Kent Island, hence it is also known as the Metapeake area of Kent Island.

The town offers diverse and exciting opportunities to its residents and visitors. Some of the best places to visit in Kent Island include Romancoke Fishing Pier, Cult Classic Brewing, Chesapeake Heritage & Visitor Center, Chesapeake Chocolates, Terrapin Beach Nature Park, Lovepoint Deli Wine & Spirits, Delmarva Balloon Rides, and more.

Would you like to spend your next vacation in Kent Island? Here are the top things to do in Kent Island, MD.

Things to Do in Kent Island

1. Matapeake Clubhouse & Beach

Matapeake Clubhouse & Beach
Credits: Forsaken Fotos / Flickr
Matapeake Clubhouse & Beach

If you truly want to explore the city, add a visit to Matapeake Clubhouse & Beach to your list of fun things to do in Kent Island, MD.

Matapeake Clubhouse & Beach is a dog-friendly location great for families to hang out and spend time together.

There is an outdoor amphitheater where visitors get to enjoy an amazing entertainment session with the series of intriguing movies and shows shown.

Matapeake Clubhouse & Beach is open throughout the year for 24 hours; there is a dog beach on the Chesapeake Bay, although dogs are not allowed at the clubhouse and beach.

There is a one-mile nature trail perfect for a quiet walk with your pet as you enjoy beautiful Chesapeake Bay views.

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

2. Kent Island Federation of Arts

Kent Island Federation of Arts
Credits: Iryna Inshyna / Shutterstock

Kent Island Federation of Arts was established in 1963 as a non-profit organization in Kent Island. The art center brings beautiful artworks to the doorsteps of people in the community and other nearby regions.

Kent Island Federation of Arts is dedicated to motivating, enhancing, and mastering every individual’s artistic creativity regardless of age.

The gallery does this by offering a wide range of art programs during summer for little children, fun fundraisers, exhibitions, courses, and other events.

In 1985, Kent Island Federation of Arts purchased a beautiful Victorian-style home currently recognized as Stevensville’s historic relic.

The structure was erected by Dr. William L. Henry in the 1900s for his wife and two sons; the Kent Island Federation of Arts is usually open from Wednesday to Sunday.

Address: 405 Main St, Stevensville, Kent Island, MD 21666, United States

3. Mark Cascia Vineyards

Mark Cascia Vineyards
Credits: True life photography / Shutterstock

Mark Cascia Vineyards is a family-owned and operated vineyard on about twelve acres of land in Kent Island.

This exceptional vineyard is known for producing a wide variety of delicious wines with great quality and uniqueness.

Mark Cascia Vineyards is a waterfront winery that offers breathtaking views of the Chesapeake Bay overlooking it.

The winery serves classic handcrafted white and red wines and dessert wines made from native varietals and vinifera grown on their own vineyard.

Mark Cascia Vineyards features a tap room where you can try out delicious samples of wines, and it is always open from 12pm-4pm on Saturdays and Sundays.

Address: 1200 Thompson Creek Rd, Stevensville, Kent Island, MD 21666-2522 United States

4. Delmarva Balloon Rides

Delmarva Balloon Rides
Credits: Steve Bower / Shutterstock

For a tremendous excitement, one of the fun things to do in Kent Island, MD is the Delmarva Balloon Rides.

Delmarva Balloon Rides offers you breathtaking views of Maryland’s Eastern Shore as you fly high in the sky.

During the rides, you go across several treetops, woodlands, rivers close by, and more, including wildlife such as birds, deer, and more.

Delmarva Balloon Rides are driven by a pilot, Todd Davis, with over twenty years in ballooning and holds a certificate of FAA Commercial Pilot.

Todd Davis also has a Class 2 medical certificate with 1200 hours of flight time; Delmarva Balloon Rides leaves you in the hands of a competent pilot to guarantees your safety.

Delmarva Balloon Rides offers rides that last sixty minutes, available in the mornings and later in the afternoon.

Address: 1137 Little Creek Rd, Chester, MD 21619, United States

5. Kent Island tour

Kent Island tour
Credits: Pavel1964 / Shutterstock

The city of Kent Island features well paved 28 miles trails frequently visited by those seeking outdoor recreational activities.

These trails include the south Island trail and the cross island route, a six-mile rail trail traveling from east to west.

The trails are ideal for biking and hiking, most especially the Cross Island Trail is an excellent trail for biking.

You will go through marshes, forested areas, and several natural resources, including nice stores where you can shop for different items.

6. Terrapin Beach Nature Park

Terrapin Beach Nature Park
Credits: Paul Watts Jr / Shutterstock
Terrapin Beach Nature Park

One of the best places to spend your day is at Terrapin Beach Nature Park, a nature preserve of two hundred and seventy-six acres in Kent Island.

Terrapin Beach Nature Park features a large number of natural resources, including wetlands of seventy-three acres.

The park features sand beaches, meadows & coastline of about 4000-feet, marshes, woodlands, an oyster walking trail of 3.25 miles, and more.

Terrapin Beach Nature Park comprises bullfrogs, swans, turtles, and ospreys, who take the park as their sanctuary.

There is a fantastic trail with notable spots that offers clearer views of the different plant species and wildlife found here.

 Terrapin Beach Nature Park provides benches along the trail where visitors can take a break and rest with a gazebo that offers breathtaking views of the Chesapeake Bay Bridge.

The park’s trail crosses numerous bridges and moves over several marshlands before going across woodlands with two points that overlook the ponds.

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

7. Historic Stevensville

Historic Stevensville
Credits: Michel G./ Flickr
Historic Stevensville

Kent Island is one city filled with lots of history, one of which is the Historic Stevensville, also known as Stevensville Historic District.

Historic Stevensville is listed on the National Register of Historic Places consisting of over one hundred buildings.

This historic district is located at Love point road just along East Main Street on a former fraction of Cockay Lane.

Historic Stevensville consists of a historic 1880 church built in the 1880s with a unique architectural pattern inspired by the Queen-Anne style.

Address: Love Point Road E Main Street, Stevensville, Kent Island, MD 21666 United States


Credits: Big Bats Cafe, Kent Island, Inc. / Facebook

Another fun thing to do in Kent Island is dining at BIG BATS CAFE, which offers mouthwatering meals.

BIG BATS CAFE was founded by Stephen F. Garland in 1997 for baseball fans and food lovers to have a good time.

Since its founding, this cafe has been a meeting spot for people in the community; people come together to eat and watch their favorite sports shows.

 BIG BATS CAFE offers an exquisitely modified menu consisting of fresh and delicious meals and amazing customer service.

They provide a vibrant and energetic atmosphere with a beautifully designed interior decorated with baseball memorabilia, including signed jerseys and baseball.

BIG BATS CAFE features large flatscreen TVs that show live sports games, which keeps the fans excited and cheerful.

Address: 216 St Claire Pl, Stevensville, MD 21666, United States

9. Lovepoint Deli Wine & Spirits

Lovepoint Deli Wine & Spirits
Credits: sama_ja / Shutterstock

A wonderful place to unwind and enjoy a drink in Kent Island is at Lovepoint Deli Wine & Spirits.

Lovepoint Deli Wine & Spirits is a highly suggested restaurant in the town and a meeting spot for many families.

They offer a wide variety of cold beer, spirits, wines, and beverages with unique tastes and immense quality.

Lovepoint Deli Wine & Spirits offers vegetarian, vegan, and gluten-free options using fresh and locally sourced ingredients.

The restaurant serves schooner, Cloverfield’s Wrap sandwiches, homemade soups, salads, and cheeses.

Love Point Deli, Wine, & Spirits staff is friendly and welcoming known for offering the best customer service.

Address: 109 Main St, Stevensville, Kent Island, MD 21666, United States

10. Dragonfly Paddle and Fitness

Dragonfly Paddle and Fitness
Credits: yurakrasil / Shutterstock

One fun thing to do in Kent Island is visiting Dragonfly Paddle and Fitness, which offers you a chance to have a great time while exercising.

Dragonfly Paddle and Fitness is open to residents and visitors alike; you don’t need any prior experience to visit.

They offer various kinds of yoga sessions for all genders, such as Yoga Barre, Hula Hoop Yoga, Beginner Yoga, Restorative Yoga, and Vinyasa Flow.

Dragonfly Paddle and Fitness offers paddleboard lessons to large groups or a single individual, and a customized paddleboard session can be created for you.

The professional instructors offer intensive training that concentrates on strength, balance, endurance, focus, and paddleboard mastery.

Dragonfly Paddle and Fitness is an excellent venue for many events like family reunions, bachelorette/ bachelor parties, corporate meetings, birthday parties, and more.

Address: 702 Reynolds Dr, Stevensville, MD 21666, United States

11. Matapeake Park

Matapeake Park
Credits: Adam Moss [CC BY-SA 2.0], Wikimedia Commons
Matapeake Park
Matapeake Park is a beautiful park in Kent Island and an awesome place for those looking to spend some quality time.

The park features a refurbished ferry house as well as a former ferry landing that serves as a fishing pier.

Matapeake Park also features a beach ideal for swimmers with glistening waters, which makes it soothing for relaxation.

There is a dog beach, and this park is home to the northern part of the well paved Kent Island South Trail, which travels from the park to Romancoke pier for approximately six miles.

Matapeake Park consists of a clean and adequately maintained amphitheater with a picnic area where you can grab lunch with your loved ones.

Address: 1112 Romancoke Rd, Stevensville, MD 21666, United States

12. Chepaseake Chocolates

Chepaseake Chocolates
Credits: k.nykyforova / Shutterstock

Are you in for some treats? Add a visit to Chesapeake Chocolates to your list of fun things to do in Kent Island, MD.

Chesapeake Chocolates was founded by the Herndon sisters-in-law in 1998, specialising in making delicious handcrafted chocolates.

This grass-root Chesapeake chocolates brand was built by experienced individuals who learnt the unique techniques used in production from Massachusetts chocolatier.

Chesapeake Chocolates come in different shapes inspired by sports, music, games, animals, and more. They offer you quality and delicious handmade treats with distinct tastes you can’t get elsewhere.

The company offers the best truffles, butter crunch, blueberry clusters, Peppermint Bark, Bipartisan Bark, Raspberry Truffles, Bushel of Crabs, and more.

Chesapeake Chocolates also offers an extensive list of Virginia wines, including Sunset White, Cabernet Franc, Chardonnay, Sunset Hills Clone 96 Chardonnay, Pinot Griggio, and more.

If you want to shop for beautiful gifts for your loved ones, Chesapeake Chocolates got you covered as they offer pottery, aprons, basket bags, necklaces, earrings, bracelets, and more.

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

13. Chesapeake Bay Sport Fishing

Chesapeake Bay Sport Fishing
Credits: BILD LLC / Shutterstock

Chesapeake Bay Sport Fishing is one of the best fishing companies in Kent Island, which takes pride in being beneficial to many businesses through its fishing services.

They offer cruise charters, and private fishing sessions for the entire family; Chesapeake Bay Sport Fishing requires fishing licenses, reels, tackle, and bait.

Chesapeake Bay Sport Fishing offers customized fishing sessions, including beverages and food, ensuring you have a fantastic day.

They offer fishing tours every week on Chesapeake Bay, so visit if you want to have an awesome time with your loved ones.

14. Taste Buds Kitchen

Taste Buds Kitchen
Credits: Taste Buds Kitchen (Chester, MD) / Facebook
Taste Buds Kitchen

Why not learn a new skill and create exciting memories in Kent Island? Visiting Taste Buds Kitchen is one of the best things to do in Kent Island, MD.

Taste Buds Kitchen offers the best culinary experience to children from as low as two years old to adults of up to ninety-nine years old.

They offer contemporary cooking classes using a multi-course menu emphasising making the meals from scratch.

Taste Buds Kitchen uses high quality and flavorful ingredients with a unique mix of spices during their cooking classes.

There are cooking camps organized for kids when the school session has ended, the kids are taught easy new recipes, make friends, and gain more confidence in the kitchen.

Taste Buds Kitchen is excellent for corporate events and parties, including get-togethers, family reunions, and more.

Address: 800 Abruzzi Dr Ste D, Chester, Kent Island, MD 21619-2382 United States

15. Chesapeake Heritage & Visitor Center

Chesapeake Heritage & Visitor Center
Credits: Kate Wagner Schleigh / Facebook
Chesapeake Heritage & Visitor Center

At the top of your list of things to do in Kent Island, MD include a visit to Chesapeake Heritage & Visitor Center, which offers a perfect guidelines of what to expect in the city.

Chesapeake Heritage & Visitor Center is a help center for visitors trying to find their way; the center offers recommendations, directions, and many other information.

This visitor center consists of a museum called the Chesapeake Legacy Museum, housed with several interactive exhibitions relating to the culture, tradition, and history of Queen Anne’s County.

Chesapeake Heritage & Visitor Center showcases rotational artworks made by passionate regional artists focusing solely on the Eastern Shore.

The staff is friendly and helpful, always willing to assist every visitor who needs it and ensuring that they leave the premises more relaxed.

Chesapeake Heritage & Visitor Center features a unique spiral staircase and an elevator that leads you to the outdoor tower, where you enjoy amazing views of the environment.

Address: 425 Piney Narrows Rd, Chester, Kent Island, MD 21619-2401 United States

16. Buzz Boutique

Buzz Boutique
Credits: Creative Lab / Shutterstock

Buzz Boutique is the number store in kent Island that offers a wide variety of merchandise for affordable prices.

This lovely store offers the best bathing products, organic & handmade soaps, fashionable clothing like cardigans & T-shirts, accessories, and more.

Buzz Boutique offers elegant clothing suitable for different events like casual hangs out, cooperate meetings, and special occasions.

Whenever you want to shop for gifts for your family and friends, visit Buzz Boutique, as you will be offered different items to pick from.

Buzz Boutique is dedicated to offering the best products with unique qualities and high durability range, making them last long.

Address: 321 Love Point Rd, Stevensville, Kent Island, MD 21666-2135 United States

17. IHOP

Credits: Olga Nayashkova / Shutterstock
Chicken Sandwiche

For an exceptional dining experience, add having a meal at IHOP to your list of top things to do in Kent Island, MD with your travel companions.

IHOP is a one-of-a-kind restaurant that offers you everything from breakfast, lunch to dinner using locally grown ingredients in their preparation.

The restaurant also offers takeout and extensive catering services, including online delivery and special hours.

IHOP offers a comprehensive food menu, including Steakburgers & Chicken Sandwiches, Family Feast, Mexican Tres Leches Pancakes, Strawberry Banana Pancakes, Belgian Waffle Combo, Boneless Buffalo Crispy Chicken Strips & Fries, Chicken & Veggie Salad, and more.

The staff ensures that everyone who walks into the restaurant is satisfied by the quality and taste of the meals plus the services rendered.

Address: 300 Abruzzi Dr, Chester, MD 21619, United States

18. Chesapeake Lights Lighthouse Tours

Credits: Chesapeake Lights Lighthouse Tours / Wiki, Public Domain

Chesapeake Lights Lighthouse Tours are perfect ways to explore the city of Kent Island; it is an eye-opening adventure where you learn things you possibly haven’t heard of.

Kent Island is home to a set of lighthouses; you will find them along the waterside and on land. If you’re a fan of lighthouses, this city is for you.

Boat trips are available at a significant spot from the structures; these trips offer you incredible views to the angles you can’t access by land.

This tours takes you back in time as you get to uncover new facts, including the reason the state of Maryland constructed the “Screwpile lighthouse.”

Chesapeake Lights Lighthouse Tours enlightens the tourists about the history of the Bay as they get a chance to interact with many well informed locals.

There are a variety of tour packages to pick from, and visitors can also customize their tour; you’re offered four various Chesapeake lighthouse tours with lots of storytelling.

19. Chesapeake Bay Charter Services

Chesapeake Bay Charter Services
Credits: Neophuket / Shutterstock

You want to have great fun? Add a visit to Chesapeake Bay Charter Services to your checklist of fun things to do in Kent Island, MD.

Chesapeake Bay Charter Services is a unique charter company that promises you exceptional moments through the series of adventures.

This full-service charter company takes its customers on a guided tour for fishing, sightseeing, and amazing dinner cruises.

Chesapeake Bay Charter Services has been in the business since 1997 and has continually offered tourists opportunities to have fun.

The company offers a wide range of dining options, from hot breakfast to cold meals prepared on-site.

Chesapeake Bay Charter Services uses different techniques in fishing, such as light tackle, live bait, and trolling.

Address: 910 Kentmorr Rd, Stevensville, MD 21666, United States

20. Cult Classic Brewing

Cult Classic Brewing
Credits: UfaBizPhoto / Shutterstock

Looking for an amazing place to chill and relax? Add a visit to Cult Classic Brewing to your list of fun things to do in Kent Island, MD.

Cult Classic Brewing is a family-friendly brewery that serves delicious and well-brewed beers made using authentic ingredients.

There is a fantastic and cozy taproom designed in a theatre-inspired style consisting of a full-service bar and restaurant.

Some drinks served include Irish Red Ale, The IPA When the Earth Stood Still, The Thirst, Island Highlander, Equals Beer (Blood Orange IPA), Amber Lager, and more.

Cult Classic Brewing also offers amazing live music performed by talented artists, which will keep you grooving and partying all night.

Address: 1169 Shopping Center Rd, Stevensville, Kent Island, MD 21666-4051 United States

21. Peace of Cake

Peace of Cake
Credits: Sergii Koval / Shutterstock
Chocolate Chip

Are you in a celebration mood or just want to enjoy a piece of cake? Add a stop at Peace of Cake to your list of things to do in Kent Island, MD.

Peace of Cake is a family owned and operated pastry store that bakes different kinds of cakes for any special event.

They use the best ingredients in the baking process to guarantee the most delicious outcome possible.

Peace of Cake decorates the cakes for special occasions with a unique mix of color and exciting designs that are out of the world.

The cakes come in different flavors like Golden Vanilla, Marble, Chocolate Chip, White, Chocolate, Apple But, Banana, Lemon, Coconut, Lemon Poppy, Spice, Carrot, Red Velvet, and more.

Peace of Cake baking crew is highly professional and experienced in the world of baking, always trying to invent something new and fresh.

Address: 314 Love Point Rd suite 101, Stevensville, Kent Island MD 21666, United States

22. Romancoke Fishing Pier

Romancoke Fishing Pier
Credits: Jarvin Hernandez / Shutterstock
Romancoke Fishing Pier

After your visit to KIFA, visiting the Romancoke Fishing Pier is one of the best things to do in Kent Island, MD with your travel companions.

The Romancoke Fishing Pier is perfect for those who love casting lines and waiting to make a big catch, as well as kayakers.

Another popular activity is crabbing during the summer months, and the pier is easily accessible from the Kent Island Bridge.

The Romancoke Fishing Pier features a kayak ramp while fishers are allowed access to a portable John.

There is a picnic area ideal for picnicking with your loved ones as you also get to enjoy dramatic views of the environment.

Address: 9700 Romancoke Rd End of Rt. 8, Stevensville, Kent Island, MD 21666 United States

23. Knoxie’s Table

Knoxie's Table
Credits: Knoxie’s Table / Facebook
Knoxie’s Table

Knoxie’s Table is a family-friendly restaurant where you and the entire can relax and enjoy a delicious meal in Kent Island.

Dining at Knoxie’s Table, a highly rated restaurant, is one of the best things to do in Kent Island, MD for an exceptional dining moment.

The homey ambiance of the restaurant gives visitors a welcoming and comfortable feeling, where they feel more like family than strangers.

Knoxie’s Table serves seasonal meals and local seafood made with special recipes and freshly sourced ingredients.

Their full-service bar offers an extensive list of drinks and an impressive selection of wines, whiskey, handcrafted cocktails, and craft beers.

Knoxie’s Table serves meals like Roasted Beet Salad, Calamari Bowl, Guacamole, Sesame Crusted Tuna, Petite Filet Mignon, Grilled Salmon, Vegetable Ramen Bowl, Roasted Exotic Mushrooms, Roasted Fingerling Potato Salad, Chilean Sea Bass, Nuts & Berries, and many others.

They provide indoor and outdoor dining with fireplaces, including an indoor and outdoor bar and booth with about one and fifty seating capacity.

Knoxie’s Table also features a more private room called DECANTER ROOM which can accommodate up to twenty-four persons, perfect for family get-togethers, corporate meetings, and other private functions, if your gathering is more than twenty-five persons, an arrangement will be made on your behalf.

Address: 180 Pier 1 Rd, Stevensville, MD 21666, United States

24. Kent Island Resort

Kent Island Resort
Credits: Kent Island Resort/ Facebook
Kent Island Resort

One of the best places to visit in Kent is Kent Island Resort. Kent Island Resort embodies country house charm and modern sophistication on the shores of Chesapeake Bay. 

The Resort also serves as a venue for weddings, business meetings, special events, family reunions, and retreats. 

At this Resort, you can eat locally sourced seasonal meals, sip champagne or enjoy acres of peaceful parklands with cycling and hiking trails and approximately 2 miles of waterfront for boating and kayaking. 

There’s also an in-ground swimming pool that is usually open every season. Their catering staff is well-seasoned and available to attend to all your food and drink needs. 

Additionally, the Resort offers excellent services and suits with unique features. Visit Kent Island Resort and be prepared to fall hopelessly in love with it. 

Address: 500 Kent Manor Dr, Stevensville, MD 21666, United States

25. Kent Island Farmers Market

Kent Island Farmers Market
Credits: leonori / Shutterstock

Are you looking for where to shop during your visit to Kent Island? If yes, why don’t you visit Kent Island Farmers Market? 

Kent Island Farmers Market is a year-round market with a wide diversity and many certified and non-certified producers. 

The market offers raw milk artisan cheese, milk, yogurt made with honey and local maple, organic ice cream, local wheat artisan bread, chicken, and free-range eggs. 

Additionally, Kent Island Farmers Market offers organic IPM-produced fruits and vegetables, chicken, vegetables, porks, grass-fed beef, different nuts and nut butter, olives and olive oil, pastries, balsamic vinegar, gluten-free baked goods, gourmet flavored hummus, and lots more. 

During winter, the market has an indoor location. 

Address: 1169 Shopping Center Rd, Stevensville, MD 21666, United States

26. DejaBlu vintage

DejaBlu Vintage
Credits: DejaBlu Vintage/ Facebook
DejaBlu Vintage

DejaBlu Vintage is an antique store in Stevensville. This store offers vintage and mid-century modern, contemporary, and seasonal furniture and accessories. 

They also offer rare pieces with characters and a story to tell; they don’t sell grandma antiques. 

The store is lovely with well-selected and impressive products and reasonable prices.

They also host a monthly weekend event called BLU, featuring newly discovered vintage and home furnishings. 

All their items are found “in the wild,” so all the events differ. The shop owner has an impressive eye for items, and the sales staff are great at their job. 

If you are a fan of antiques, make sure you pay a visit to Vintage. 

Address: 311 Love Point Rd, Stevensville, MD 21666, United States

Planning a Maryland road trip? here is a guide on fun things to do in Columbia and things to do in Hagerstown for a fun trip.

Plan a trip to Kent Island

Kent Island is an extremely beautiful city featuring several amazing attractions filled with fascinating history and culture.

When you’re visiting a beautiful city like Kent Island, make sure you come along with your camera, because you would definitely love to capture all the beautiful attractions you visit.