Things to do in Chester

Find and book activities, attractions and tours

Chester

Chester Attractions

There's something endearing about smaller cities. Whether you're on your way to Chester for a couple of days or you're thinking of staying longer, you'll easily fall in love with this destination. In fact, with so many wonderful things to do and awesome attractions to see, you might never want to leave!

Find out what makes Chester tick with the most popular tours & day trips. Check out our top {6 fun activities in Chester fun activities in Chester}, and rest easy knowing that we offer free cancellation and no added fees.

Things to do

Epiphany

2 Hour Chesapeake Day Sail on Catamaran Epiphany

$245
per adult
2 Hour Chesapeake Day Sail on Catamaran Epiphany
2-Hour Relaxing Chesapeake Day Sail on Lady Patty

2-Hour Relaxing Chesapeake Day Sail on Lady Patty

$160
per adult
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
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What to do in Chester

Things to Do in Chester with Kids

You'll find plenty of fun activities to do with the kids in and around Chester. Keep everyone happy with our family friendly experiences.

 

Looking for sports, concerts, or theater events in Chester? Search event tickets to see what's happening today, or to plan what to do this weekend!

 

 

Discover the most popular places to visit in Chester

Chesapeake Exploration Center

Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.

Chesapeake Exploration Center

 

Looking for fun things to do nearby? Check things to do near me to find and book the best things to do, fun activities, and top attractions wherever you happen to be.

 

 

Popular day trips from Chester

Aerial view of Kent Narrows peninsula inlet on Chesapeake in Grasonville Maryland, beach houses with private long docks for the sailboats line a road curving like an S shape with blue sky and water

Grasonville

Matapeake Fishing pier on the Chesapeake Bay in,Stevensville, Queen Anne's County, Maryland

Stevensville

Frequently asked questions

Is Chester worth visiting?
One of the most popular things to do in Chester is visit Sandy Point Beach. Check this top sight off your itinerary, then discover more of this area's watersports and history.
How do I spend a day in Chester?
Sandy Point Beach and Bay Ridge Beach are two excellent places to begin your vacation adventures. Be sure to explore the dining and retail options in Chester while you're in town too.
What is the top tourist attraction in Chester?
Sandy Point Beach is one of the top tourist attractions in Chester and should be high on every to-do list of the area.
Is three days enough to stay in Chester?
Three days in Chester is plenty of time to enjoy the city's leading attractions. Many travelers book for two days on average. Matapeake State Park, Love Point State Park and Chesapeake Bay Environmental Center are top-rated sights. Like to discover more? Stick around a bit longer to explore nearby hotspots such as Baltimore.
Is Chester a walkable city?
With major attractions like Paul Reed Smith Guitars nearby, Chester is every bit a place to experience on foot. Want to discover some hip neighborhoods a walkable distance from downtown? Kent Narrows is just 3 miles away.
What are some activities to do in Chester with kids?
Whether you're vacationing with young explorers or adventure-seeking teens, an itinerary filled with fun activities makes all the difference. Check out our recommendations for what to do in Chester with kids.

What to do in Chester for adults?
Paul Reed Smith Guitars is one of the top things to do in Chester. With loads of activities available, there's something here for everyone to experience.
Are there free things to do in Chester?
From relaxing in parks to strolling around vibrant neighborhoods, it's simple to discover free things to do in Chester. If you're in need of ideas, ask for recommendations from a local tour guide. Matapeake State Park is a great spot for anyone planning to save on their sightseeing adventures.