Historic Summer Bucket List Challenge

The Chesapeake Crossroads Heritage Area invites you to take part in our 2025 Historic Summer Bucket List Challenge — a fresh take on summer fun that combines learning, adventure, and memory-making.

From art exhibits to archaeology, hikes to historic houses, outdoor concerts to waterfront fun, this is not your average summer checklist. Activities are happening this summer at sites across the Chesapeake Crossroads Heritage Area where you can experience our region’s most exciting cultural, natural, and historic sites.

DOWNLOAD YOUR BUCKET LIST BINGO CARD

How to Join The Challenge

Download your Bucket List Bingo Card (or pick one up at a participating site.)
Complete as many activities as you can between now and August 31, 2025.
Snap a picture at one of your stops and post your completed Bingo Card on our Facebook page.
Bonus: Tag your favorite sites to spread the love and inspire others to join in!

We will recognize the first 20 people or families that complete the 2025 Historic Summer Bucket List Challenge on our website– AND we’ll send them a Chesapeake Crossroads Heritage Area gift!

Scroll Down- So many to choose from!

Annapolis Maritime Museum

Annearundell Free School

Banneker-Douglass-Tubman Museum

Captain Avery Museum

Chesapeake Children's Museum

Frederick Douglass Museum

Galesville Heritage Society

Historic Village Museum (Deale)

Historic London Town And Gardens

Maryland State Archives

Maryland State House

Museum of Historic Annapolis

National Cryptological Museum

Naval Academy Museum

Odenton Heritage Society Museum

Woodlawn History Center (at SERC)

Meander at a
MUSEUM

Programs are underway to commemorate the 250th anniversary of the founding of our Nation and the events that lead up to– and resulted from– the Revolutionary War.

Annapolis 250 Commission

MD250 Commission

Revolutionary London Town Weekend!

Visit Annapolis& Anne Arundel County Calendar of Events

What's a
SEMIQUINCENTENNIAL
anyways!?

(Hint– 250 years ago!)

Enjoy live music outdoors all summer long!

Carr's Beach Reunion : June 19th

Music on the Lawn at Captain Avery

Goshen Farm Preservation Society Summer Concert Series

Annapolis Maritime Museum Tides & Tunes

Annapolis City Dock

Quiet Waters Park Concerts

Bayside Summer Concert Series at Downs Park

Enjoy an
OUTDOOR
CONCERT

Juneteenth celebrates June 19 1865- the end to slavery in the United States.

Celebrate
JUNETEENTH

Get your hands on Heritage and the Environment

Get your
hands
DIRTY!

Weeknight races can be seen from the shoreline of Annapolis or Galesville on the West River on Wednesdays and Fridays. Head out to get a good spot around 5 or 6 o'clock!

Both the Skipjack Wilma Lee & Schooner Woodwind will get you up close to the action on Wednesday nights.

Spots to watch from shore in Annapolis include Annapolis City Dock, The Eastport Bridge, public street end parks in Eastport, and Elktonia Beach.

The races in Galesville/ West River can be seen from the County Wharf or grab a table and watch from at Pirates Cove or Stan & Joe's Riverside.

WATCH
Weeknight
Sailboat Races

Explore Military History

Learn
About the
MILITARY &
SPYCRAFT

Come together to celebrate local traditions, culture, and community.