Kent Island Travel Guide

Discover the best things to do, places to visit, and local culture of Kent Island, Maryland in this comprehensive travel guide.

Introduction to Kent Island

Situated on the Eastern Shore of Maryland, Kent Island offers a perfect combination of outdoor adventures, cultural and historical attractions, and scenic views. The island, which is the largest in Chesapeake Bay, offers a lot to visitors, from hiking and biking trails, kayaking and fishing opportunities, to museums, art galleries, and local wineries.

List of Places to Visit in Kent Island

Culturally Important Attractions: Museums and Historical Places

Chesapeake Bay Exploration Center and Museum

This museum, located close to the entrance to Kent Island, offers an interactive and engaging exhibition on the culture, heritage, and ecology of Chesapeake Bay. Visitors can learn about the lives of watermen, how Chesapeake Bay formed, and how it has changed over time.

Kent Island Federation of Art

For art enthusiasts, the Kent Island Federation of Art is a must-visit place. It is a non-profit organization that supports and promotes local artists. Visitors can appreciate the art pieces displayed in the gallery and attend art workshops and events.

Stevensville Train Depot

Travel back in time by visiting the Stevensville Train Depot, one of the oldest depots in Maryland. It is now a museum featuring collections of artifacts and memorabilia from the Chesapeake Beach Railway Company, which operated from 1898 to 1935.

Natural Attractions of Kent Island: Outdoor Adventures and Scenic Views

Terrapin Nature Park

Terrapin Nature Park is a natural gem located on the Chesapeake Bay. It offers hiking trails with scenic views, beaches, and picnic areas. The park is an excellent place for bird watching and wildlife viewing, as it is home to over 200 species of birds and other animals, including deer, foxes, and ospreys.

Matapeake Beach and Park

Matapeake Beach and Park offers a beautiful, sandy beach, perfect for swimming and sunbathing. The park also has tennis courts, a playground, and several picnic areas. Visitors can also take a stroll on the nearby pier to enjoy breathtaking views of Chesapeake Bay and watch the boats go by.

Kent Island South Trail

For hiking and biking enthusiasts, the Kent Island South Trail is a must-visit. The trail is four miles long, and it offers scenic views of Chesapeake Bay and Terrapin Nature Park.

Hiking/Biking Routes of Kent Island

In addition to the Kent Island South Trail, hiking and biking enthusiasts can also explore the Cross Island Trail, a 6-mile trail that offers a scenic view of the Chesapeake Bay Bridge and the nearby Kent Narrows.

Best Things to Do in Kent Island: Activities and Tours

Fishing Tours

Kent Island is known for its excellent fishing opportunities. Visitors can join fishing tours and catch striped bass, bluefish, and other fish.

Kayaking and Paddleboarding

Visitors can rent kayaks and paddleboards or take group tours to explore the waters of Chesapeake Bay.

Wine Tasting Tours

Kent Island is home to several local wineries where visitors can taste and learn about the production of Maryland wines.

Week-Long Itinerary for Kent Island

Day Activity
1 Visit Chesapeake Bay Exploration Center and Museum
2 Hike Kent Island South Trail
3 Take a Fishing Tour
4 Visit Stevensville Train Depot and Kent Island Federation of Art
5 Visit Terrapin Nature Park
6 Rent a Kayak or Paddleboard
7 Wine Tasting Tour

Food and Drink Scene of Kent Island

Must-Try Dishes

Crab Cakes

Being close to the Chesapeake Bay, Kent Island is known for its delicious crab cakes, which are made from the freshest local seafood.

Smith Island Cake

This dessert is the official state dessert of Maryland. It is a 10-layered cake made with buttercream icing.

Local Beverages

Chesapeake Bay Wine Trail

Visitors can enjoy wine tasting and vineyard tours in the several local wineries.

Blackwater Distillery

Blackwater Distillery is a local distillery offering rum, gin, and vodka made from local ingredients.

Where to Stay in Kent Island: Hotels, Hostels, and Guesthouses

Kent Island offers a wide range of accommodations to suit all budgets and preferences. From luxurious hotels, family-friendly guesthouses, to budget-friendly inns. Some of the top-rated hotels in Kent Island are The Inn at Chesapeake Bay Beach Club, The Hilton Garden Inn, and The Kent Manor Inn.

What to Buy in Kent Island: Souvenirs and Local Products to Bring Home

Visitors can bring home local souvenirs and products, including local wines, seafood, art pieces, and memorabilia from the Chesapeake Beach Railway Company.

Local Culture and Customs of Kent Island

Kent Island has a rich history and cultural heritage that is reflected in its art, music, and festivals. The island hosts several annual events such as the Chesapeake Bay Blues Festival, Kent Island Day, and Terrapin Nature Park Fall Festival.

Best Time to Visit Kent Island

The best time to visit Kent Island is from late spring to early fall when the weather is mild and pleasant. Visitors can enjoy outdoor activities, festivals and events, and scenic views of the Chesapeake Bay.

Do’s and Don’ts of Kent Island


  • Explore the outdoor adventures and scenic views of Kent Island.
  • Try local seafood and wine.
  • Attend local festivals and events.


  • Litter or harm the environment.
  • Ignore local customs and behavior.

Safety and Health

Safety in Kent Island

Kent Island is a safe destination and has a low crime rate. Visitors should still take standard precautions and secure their belongings, especially when in crowded or touristy areas.

Health in Kent Island

Visitors should bring sunscreen and insect repellent, especially if they plan to enjoy outdoor activities. It is also important to stay hydrated and be aware of the symptoms of heat exhaustion.

Getting to Kent Island: Transportation Options and Logistics

Airports Near Kent Island

  • Baltimore/Washington International Thurgood Marshall Airport (BWI)
  • Ronald Reagan Washington National Airport (DCA)

Bus Stations Near Kent Island

  • Annapolis Bus Station

Other Options

  • Driving: For visitors who plan to drive to Kent Island, it is easily accessible via Route 50.
  • Ferry: Visitors can take a ferry from Sandy Point State Park to Kent Island.

How to Get Around in Kent Island

Visitors can rent a car or bike to explore Kent Island. There are also several taxi services and rideshare options available.

Where to Go Next from Kent Island: Nearby Destinations and Excursions

  • St. Michaels: A picturesque town on the Eastern Shore featuring historic homes, boutiques, and waterfront restaurants.
  • Annapolis: The state capital of Maryland, it is known for its colonial architecture, maritime heritage, and the United States Naval Academy.
  • Baltimore: A bustling city known for its rich history, architecture, and cultural arts.


Kent Island offers a perfect combination of outdoor adventures, cultural and historical attractions, and scenic views. Visitors can enjoy hiking and biking trails, kayaking and fishing opportunities, local wineries, art galleries, and museums. The island has a rich history and cultural heritage reflected in its festivals and events. Plan your trip to Kent Island and experience all that this beautiful destination has to offer.