Top Things to Do in Chesapeake Bay

The Chesapeake Bay is packed with history, scenery, and family-friendly attractions that make it a great destination beyond time on the water. Whether you’re visiting before or after your trip with Wanna Be Angler, exploring local sights adds even more value to your stay. From waterfront towns to historic landmarks, there are plenty of memorable things to do in Chesapeake Bay that appeal to couples, families, and first-time visitors.

Below are some of the top Chesapeake Bay attractions and activities to enjoy while you’re in the area.

Explore Historic Annapolis

Annapolis is one of the most popular stops for visitors looking for classic Chesapeake Bay culture. Walk through the historic downtown area, tour the Maryland State House, or stroll along brick-lined streets filled with shops and cafes. The city’s deep maritime roots make it a must-see for anyone interested in local history.

Families enjoy the relaxed pace and waterfront views, while history lovers appreciate the preserved architecture. Annapolis is also a great spot for dining and people-watching after a day outdoors.

Visit Chesapeake Bay Maritime Museums

Learning about the Bay’s working heritage adds context to everything you see on the water. Maritime museums throughout the Chesapeake Bay region highlight boatbuilding, crabbing traditions, and the communities shaped by the estuary.

These museums are excellent Chesapeake Bay family activities, offering interactive exhibits and hands-on displays that keep kids engaged while adults learn about local culture.

Enjoy Waterfront Dining

One of the simplest pleasures is dining along the water. Chesapeake Bay waterfront restaurants offer fresh regional flavors, relaxed settings, and scenic views that make meals feel special.

From casual crab houses to sit-down restaurants, dining out is a favorite activity for visitors staying near Edgewater, Annapolis, and other Bay towns. It’s an easy way to unwind before or after your trip with Wanna Be Angler.

Walk or Bike Bayfront Trails

The Chesapeake Bay area features several walking and biking trails with water views, wildlife sightings, and shaded paths. These trails are ideal for morning walks, light exercise, or family outings that don’t require planning.

They’re especially popular with visitors looking for low-key Chesapeake Bay attractions that balance outdoor time with relaxation.

Visit Local Parks and Beaches

Public parks and small beaches along the Chesapeake Bay provide space to relax, picnic, and enjoy the scenery. Many locations have playgrounds, open lawns, and calm shorelines suitable for families.

These areas are perfect for downtime and are often close to towns like Edgewater and Annapolis, making them easy to add to your itinerary.

Discover Local Shops and Art

Small towns around the Chesapeake Bay are known for local art, handmade goods, and boutique shopping. Exploring these areas gives visitors a chance to support local businesses and find unique souvenirs.

It’s also a great way to slow down and experience the personality of the region between planned activities.

If you’re planning a visit, pairing local attractions with a guided trip creates a well-rounded experience. Book your time on the water with Wanna Be Angler, then enjoy everything else the Chesapeake Bay has to offer for a trip filled with variety, comfort, and lasting memories.