Things to do in Chester

Activities, attractions and tours

A boat docked at a pier during twilight with a city skyline in the background.

Things to do

St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany

St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany

S$343
per adult
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany
St. Michaels: 2-Hour Wine Tasting on Sailing Cruise Epiphany

St. Michaels: 2-Hour Wine Tasting on Sailing Cruise Epiphany

S$378
per adult
St. Michaels: 2-Hour Wine Tasting on Sailing Cruise Epiphany
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty

St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty

S$202
per adult
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty
Epiphany

2 Hour Chesapeake Day Sail on Catamaran Epiphany

S$311
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

S$203
per adult
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
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What to do in Chester

Stay near popular Chester attractions

Chesapeake Exploration Center

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

Is Chester worth visiting?
Providing a blend of watersports and history, there's no shortage of things to do in Chester. While you're here, check out Sandy Point Beach, a leading attraction in the area.
How do I spend a day in Chester?
When you've checked off key attractions like Sandy Point Beach and Bay Ridge Beach, spend some time exploring the food and retail options in Chester.
What is the top tourist attraction in Chester?
Don't go home without visiting Sandy Point Beach, rated the top tourist attraction in Chester.
Is three days enough to stay in Chester?
You can easily tick off top attractions like Matapeake State Park, Love Point State Park and Chesapeake Bay Environmental Centre with a three-day trip to Chester. On average, most travellers plan two days here. There's plenty to see and do nearby too, so stick around longer and head to Baltimore.
Is Chester a walkable city?
It depends on what you plan to see and do in Chester. Several leading attractions, like Paul Reed Smith Guitars, are reachable on foot. If you feel like a stroll through one of Chester's neighbourhoods, Kent Narrows is 5 kilometres away from downtown.
What are some activities to do in Chester with kids?
If you're looking for activities and attractions for all ages, check out these fantastic ideas for what to do in Chester with kids.
What to do in Chester for adults?
There are lots of things to do in Chester, with experiences for adults of all ages. Finish your day off at Paul Reed Smith Guitars.
Are there free things to do in Chester?
In Chester, Matapeake State Park is a must-see spot for anyone looking to enjoy the city without taking their wallet out. Also, stroll around the local neighbourhoods and parks, and ask a local tour guide for ideas. It's a simple way to find out about the best free things to do in Chester.