Visit Annapolis, MD | Plan Your Trip To Chesapeake Bay

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There’s something special about taking your time in Annapolis and Anne Arundel County, Maryland. Home to the Maryland State House and the United States Naval Academy, Annapolis blends rich American history with a walkable downtown, waterfront views, and a lively food and culture scene. Visitors can explore the Historic District, enjoy locally owned cafés and restaurants, and take in the Chesapeake Bay from City Dock and nearby marinas.

Beyond downtown Annapolis, Anne Arundel County, MD offers even more to experience. The destination is easily accessible via Baltimore/Washington International Thurgood Marshall Airport (BWI) and features major attractions like Live! Casino & Hotel Maryland, outdoor recreation at Sandy Point State Park, and a year-round lineup of music festivals, live entertainment, and food festivals. Whether you’re planning a weekend getaway or a longer stay, Annapolis and Anne Arundel County deliver history, entertainment, and coastal charm all in one place.

 

Upcoming Events Sailing

What's Making Waves in 2026?

Make 2026 your year to explore Annapolis and Anne Arundel County. Sail the Chesapeake, savor local flavors, and dive into seasonal events and experiences with our curated travel guides and must-do itineraries.

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Annapolis and Anne Arundel 250

​As the 250th anniversary of the signing of the Declaration of Independence approaches, Annapolis and Anne Arundel invites you to immerse yourself in the rich history of 1776. Stroll the same cobblestone streets once walked by George Washington, dine in historic taverns frequented by Thomas...

Details Seafood dip with a cheddar cheese pull of creamy seafood from a black cast iron pan.

Annapolis Restaurant Week

Annapolis has totally become a foodie paradise, and this event is the perfect chance for anyone who loves to eat to dive in. With over 30 restaurants serving up their best dishes, it’s a great way to finally check out that hidden spot you've been eyeing or treat yourself to some local favorites.

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Adventures For Every Season

St. Patricks Day Parade

St. Patrick's Parade and Festival

Annapolis Film Festival 2025

Annapolis Film Festival

Sailboats and catamarans lined up in the water with flags flying up the mast.

Annapolis Spring Sailboat Show

Maryland flag in yellow and red

Maryland Day

May Day

May Day in Annapolis

Blue Angel air show flying in 5 opposite directions over U.S. Naval Academy

Commissioning Week

Worlds Largest Crab Feast

Annapolis Crab Feast

Kim Hovell oyster paintings

Annapolis & Anne Arundel County Arts Month

Singers performing at Let's Go Music Festival

Let's Go! Music Festival

Image of people in Renaissance era clothing dancing at the Maryland Renaissance Festival

Renaissance Festival

Artist painting

Paint Annapolis Plein Air Festival

4th of July Boating Event

4 th Of July Weekend

crowd of music lovers at Annapolis Songwriters Festival

Annapolis Songwriters Festival

Navy Football Stadium, Midshipmen line up on the field before a game

USNA Football

a bird's eye view of the Annapolis Baygrass Festival at Sandy Point State Park

Annapolis Baygrass Festival

Three black men singing on a stage at a festival

Kunta Kinte Heritage Festival

Blue building with a giant pumpkin in front

Great Annapolis Pumpkins

A man holds out a Maryland Blue Crab

Maryland Seafood Festival

two men in Medeival garb at a renaissance festival

Renaissance Festival

Aerial view of Annapolis harbor during sailboat show with loads of  boats looking out across the water to the Chesapeake Bay

United States Boat Shows

People march in the Annapolis Pride Parade holding banneres and signs about LGBTQIA+ rights

Annapolis Pride Parade & Festival

Navy Marine Corps Stadium field on game day at Military Bowl 2019

Military Bowl

Annapolis Chocolate Binge Festival

Annapolis Chocolate Binge Festival

Eastport Yacht Club Parade

Eastport Yacht Club Lights Parade

Grand Illumination

Grand Illumination

Midnight Madness

Midnight Madness

People at a holiday market

Annapolis Holiday Market

Participant with hands up in purple jacket is excited to be racing at Bay Bridge Run

Bay Bridge Run

Lights on the Bay

Lights on the Bay

Snowflake Alley

Snowflake Alley

Explore Our Neighborhoods

Ariel view of Annapolis City Dock with sunset and clouds

City Dock

Main Street, Annapolis

Main Street

Eastport

Eastport

West Annapolis Petticoat

West Annapolis

State Circle/Maryland Avenue

Maryland Avenue

A sunset shot of Live! Casino & Hotel

Arundel Mills

Things To Do in Annapolis and Anne Arundel County

People playing craps in a casino

BWI & Arundel Mills Entertainment District

Nutcracker - Ballet Theatre of Maryland

Arts & Entertainment

Maryland Avenue Shopping

Shopping

Guinness - Open Gate Brewery

Breweries & Pubs

Arundel Mills - A Shopping Center

Arundel Mills

View All Things To Do Candlelight: Valentine’s Day Special

Candlelight: Valentine’s Day Special

Black Violin: Full Circle Tour

Black Violin: Full Circle Tour

Annapolis Restaurant Week

Annapolis Restaurant Week

Annapolis Logo Stamp 6 Most Popular Blog Posts Read All Blog Posts An aerial view of Annapolis looking from the water to the Maryland State House

Top 25 Things To Do In Annapolis

A brown parchment lined table with mallets and steamed crabs, shrimp and hushpuppies on the table.

Food Festivals in Annapolis & Anne Arundel County

Seafood dip with a cheddar cheese pull of creamy seafood from a black cast iron pan.

The Top 10 Foods You Must Try in Annapolis, Maryland

Let's Go Music Festival 2024

Music Festivals in Annapolis, Maryland

St. Patricks Day Parade

St. Patrick’s Day Bars in Annapolis

Great Frogs Wine

FeBREWary in Annapolis and Anne Arundel County

Read All Blog Posts

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View / Download The2026 Visitor Guide

This handy resource includes a complete listing of accommodations, restaurants, shopping destinations, and more in Annapolis and Anne Arundel County!

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Stay inspired all year long with The Chesapeake Charm, your go-to guide for planning unforgettable Annapolis & Anne Arundel County adventures.

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