Experiences

see all

Points of Interest

see all

SUGGESTED ITINERARIES

see all
  1. The Chesapeake Experience

    Experiencing the Chesapeake is all about getting your feet wet, tasting its flavors, and learning about its history.

top events

see all

By Month

see all
FULL EVENT CALENDAR

featured event

Holiday Events Holiday Events

Select a Category

GETTING AROUND

RESOURCES

Select a Category

PLANNING

RESOURCES

Not sure what you’re looking for?

Try typing in a phrase above, and we’ll make suggestions to get you back on course.

RECOMMENDED SEARCHES
upcoming events

MONTHLY EVENTS

Looking for the best time to come to Annapolis? Learn more about local events by selecting a month below.

January
January

Get out of the chilly weather this January and enjoy the art and dining scenes in Annapolis.

LEARN MORE
February
February

Ranked one of America’s Most Romantic Towns by Travel+Leisure Magazine, Annapolis is a great place to spend time in February.

LEARN MORE
March
March

Winter is coming to an end, and March is a wonderful time to beat the crowds and get a taste of the unique character of Annapolis.

LEARN MORE
April
April

Spring has arrived! Get out on the water, dine outside, join a tour, or take part in the many events happening in April.

LEARN MORE
May
May

From Blue Angel Flight demonstrations to food-packed events, May in Annapolis is all about being outside.

LEARN MORE
June
June

As summer rolls in, come enjoy Annapolis’ art, dining, history, on the water activities, and the many festivals and events in June.

LEARN MORE
July
July

July's sunny weather encourages locals and visitors alike to enjoy the area’s outdoor activities, events, and festivals.

LEARN MORE
August
August

Visiting Annapolis in August means one thing: Get out on the water! Climb aboard a sailboat or rent a kayak/paddleboard and cool off in the breeze.

LEARN MORE
September
September

Fewer crowds and cooler weather in September makes for a perfect weekend getaway in Annapolis.

LEARN MORE
October
October

Fall is here and so are the area’s seasonal festivals: Hayrides, haunted tours, and family-friendly events.

LEARN MORE
November
November

Rated one of the best cities for the holidays by Travel+Leisure, Annapolis in November is a great way to kick start the season.

LEARN MORE
December
December

With the holiday season in full swing, Annapolis is the perfect destination to find a special gift for everyone on your list.

LEARN MORE