America's 250th

Your Harborfront Home Base

Set directly on the water beside City Dock, Annapolis Waterfront Hotel places you at the center of Annapolis life. Sailboats drift across Spa Creek, dockhands call across the harbor, and the scent of world-famous Chesapeake crab cakes drifts from nearby kitchens.

Step outside and you’re within minutes of the shops and cafés of downtown, the historic homes of Maryland’s Declaration signers, and the waterfront paths connecting Annapolis to Eastport. Or, head to the South River to visit Historic London Town and Gardens, a former colonial port where gardens, archaeology, and the restored William Brown House bring the 18th century to life.

After a day exploring, return to harbor views, fresh coastal flavors, and the easy rhythm of a port city that has welcomed travelers for centuries.

Annapolis 250 Events & Experiences

In 2026, Annapolis and Anne Arundel County will commemorate America’s 250th anniversary with festivals, exhibitions, sailing traditions, and historic reenactments across the Chesapeake region.

Maryland Day Celebration
March 19–25, 2026
Historic sites across Anne Arundel County open their doors with tours, lectures, and living history programs honoring the founding of Maryland.

Annapolis Film Festival
March 26–29, 2026
Downtown theaters and galleries host international films, premieres, and filmmaker panels during this lively spring festival.

Naval Academy Commissioning Week

May 20-22, 2026

One of Annapolis’s most anticipated traditions, Commissioning Week celebrates the graduation of midshipmen at the United States Naval Academy. The week includes ceremonies, concerts, and the famous Blue Angels flyover above the Severn River.

Annapolis Spring Sailboat Show
April 24–26, 2026
For decades, the Annapolis Boat Shows have drawn sailors from around the world to City Dock. Hundreds of sailboats, gear demonstrations, and maritime showcases transform the harbor into one of the largest sailing exhibitions in the country.

Annapolis 250 Independence Celebration
July 4, 2026
A citywide celebration honoring the nation’s anniversary with harbor festivities, a naturalization ceremony, cultural programming, and fireworks over Annapolis Harbor.

Annapolis Rotary Crab Feast
August 7, 2026

Crack, pick, and savor one of Maryland’s most beloved traditions. Known as the world’s biggest crab festival, the Annapolis Rotary Crab Feast gathers thousands each summer for piles of Chesapeake Bay blue crabs, corn on the cob, and cold drinks. Hosted by the Rotary Club of Annapolis, the event supports community charities while celebrating the region’s most iconic seafood.

Kunta Kinte Heritage Festival

August 7-9, 2026

This annual festival celebrates African American history and culture through live music, storytelling, food, and community gatherings. Named for the character from Roots, the exciting event honors the heritage of the Chesapeake region and its ties to the African diaspora.

U.S. Powerboat Show
October 8–11, 2026
Every October, Annapolis Harbor transforms into an active marina filled with the newest motor yachts, marine gear, and boating innovations. The U.S. Powerboat Show draws enthusiasts from across the country for dockside demonstrations, educational seminars, and the chance to step aboard hundreds of boats in the heart of downtown.

U.S. Sailboat Show
October 15–18, 2026 | City Dock
Known worldwide among sailors, the Annapolis Sailboat Show showcases everything from sleek racing vessels to family cruisers. Floating docks fill the harbor with sailboats, gear displays, and hands-on seminars, making it one of the largest and longest-running in-water boat shows in the country.

Drink Like a Revolutionary Tavern Trail
Year-round 2026
Follow the footsteps of early American leaders through historic taverns like Middleton Tavern and Reynolds Tavern, where figures such as George Washington and Thomas Jefferson once gathered to debate the future of the colonies.

She Speaks: Black Women Artists and the Power of Historical Memory
Through January 16, 2027 | Banneker-Douglass-Tubman Museum

This powerful exhibition explores 250 years of American history through the work of contemporary Black women artists. Featuring painting, photography, textiles, installation, and more, She Speaks highlights the role Black women have played in shaping and preserving the nation’s story.

Plan Your Visit

From the waterfront, Annapolis can be easily explored on foot. Stroll through the nationally-landmarked streets of the Colonial Historic District, boasting the highest concentration of Georgian-style brick buildings in the country. Cross the bridge to the maritime community of Eastport where the Annapolis Maritime Museum & Park overlooks Back Creek and sailboats gather near the docks of the Eastport Yacht Club. Or, follow the harbor paths along Spa Creek to Susan Campbell Park and Ego Alley, and watch sailboats glide across the harbor toward the United States Naval Academy.

Nearby highlights include waterfront parks along the Chesapeake Bay like Horn Point Park, which marks the site of a Revolutionary War fort that once protected Annapolis Harbor, as well as the scenic trails of Quiet Waters Park and views of the iconic Thomas Point Shoal Lighthouse standing watch over the Bay.

Transportation Tips

Walking: Downtown Annapolis is compact and easy to explore on foot, with historic streets, shops, and waterfront views just steps apart.
Water Taxi: Seasonal water taxis connect City Dock with Eastport and marinas along Spa Creek and Back Creek.
Driving: Scenic routes across Anne Arundel County, including the Roots & Tides Scenic Byway, lead to waterfront villages, historic sites, and Chesapeake Bay landscapes.

Be Part of the Celebration

America’s 250th anniversary will be marked across the country. In Annapolis, it feels woven into everyday life; in the harbor views, the historic taverns, and the streets where early leaders once gathered over revolutionary ideas.

Life in Annapolis has always revolved around the water. From its harborfront setting, Annapolis Waterfront Hotel offers a natural starting point for exploring the city’s historic streets, sailing traditions, and Chesapeake flavors. During America’s 250th anniversary, it’s an easy place to settle in while discovering the stories that still live here.