Nestled along the shimmering shores of the Chesapeake Bay, Annapolis, Maryland dazzles as one of the East Coast's most picturesque and vibrant small cities. Steeped in centuries of maritime history and bursting with contemporary flair, Annapolis is a place where cobblestone streets wind past colonial mansions, sailboats bob rhythmically in historic harbors, and the aroma of Old Bay-spiced seafood fills the waterfront air. The wide variety of things to do in Annapolis makes it a true traveler's paradise—whether you crave unforgettable food experiences, want to delve into rich American history, or simply seek out scenic adventures on land or water.
With so many things to do in Annapolis, your days can be as packed or as leisurely as you wish. Savor local Chesapeake cuisine at award-winning restaurants, immerse yourself in world-class museums, or catch live music echoing from boisterous pubs along Main Street. Outdoor lovers will find endless opportunities for kayaking, sailing, and hiking, while festival-goers can dance the night away at legendary local celebrations. From boutique shopping to stadium sports, the list of things to do in Annapolis is as diverse as the city’s storied past and energetic present. Ready to chart your perfect getaway? Let’s dive into Annapolis’ most unmissable experiences.
Food & Drink in Annapolis
No guide to things to do in Annapolis would be complete without a savory detour through its incomparable food scene. The city’s location along the bountiful Chesapeake Bay means that blue crabs, oysters, and fresh fish are staples at many of Annapolis' beloved eateries. Begin your culinary adventures at the iconic Cantler’s Riverside Inn, a rustic crab house tucked away on Mill Creek where locals and visitors alike happily crack open steaming hot crabs right on paper-covered tables. Here, you’ll hear the rhythmic tap of mallets and the laughter of families while savoring the savory tang of Old Bay seasoning, perfectly paired with a cold local brew.
For those seeking refined waterfront dining, Chart House delivers a magical combination of panoramic harbor views and expertly prepared seafood. Sip a hand-crafted cocktail while the sun dips behind the masts at Spa Creek, or indulge in their legendary prime rib and coconut shrimp. Just steps away, Blackwall Hitch offers a modern twist on nautical chic, with a lively menu spanning Chesapeake Bay oysters, flatbreads, and creative cocktails best enjoyed on their open-air patio.
Annapolis’ love affair with food goes beyond seafood. At Iron Rooster, breakfast is served all day, and few locals can resist their homemade pop-tarts or the signature “Roostart.” If a farm-to-table ethos is your jam, Level – A Small Plates Lounge serves up inventive shareable dishes crafted from locally sourced ingredients, all within a cozy, brick-walled setting on West Street’s bustling arts corridor. Beer lovers should pop into Forward Brewing in Eastport for small-batch ales and imaginative bites, while wine enthusiasts will adore the global selections at Red Red Wine Bar.
Don’t forget the sweet side of things to do in Annapolis! Annapolis Ice Cream Company churns out small-batch, hand-crafted flavors like Maryland Mud and Cinnamon Oatmeal Cookie, a summertime favorite for strolling Main Street. Meanwhile, the intoxicating aroma from Kilwins Annapolis draws dessert lovers in for rich fudge, caramel apples, and house-made chocolates.
Tip from a local: “Get your crabs early at Cantler’s on weekends—by noon, there’s usually a line out the door, especially during the season,” advises Annapolitan foodie Josh W.
Best Museums in Annapolis
For history buffs and curious wanderers alike, exploring the museums is among the top things to do in Annapolis. Start your journey at the magnificent U.S. Naval Academy Museum, located right within the storied U.S. Naval Academy. Here, centuries of naval history come to life through rare artifacts, model ships, and the stirring “Life and Death at Sea” gallery. The Academy campus itself is a living museum—don’t miss the awe-inspiring Chapel and the crypt of John Paul Jones.
Just steps from the water, the Annapolis Maritime Museum & Park immerses visitors in the city’s seafaring heritage. Interactive exhibits detail the lives of Chesapeake Bay watermen, the ecology of the oyster industry, and Annapolis’ pivotal role as a sailing capital. The museum’s waterfront campus in Eastport includes a restored skipjack and hands-on activities for kids—making it a favorite among families seeking educational things to do in Annapolis.
For a deep dive into African American history, the Banneker-Douglass Museum stands as Maryland’s official museum of African American heritage. Housed in a beautifully restored 19th-century church, the museum showcases exhibitions on Frederick Douglass, Harriet Tubman, and the enduring legacy of Black Marylanders. Art shows, lectures, and community events unfold here throughout the year, providing vital context to Annapolis’ cultural fabric.
Art aficionados should not miss the Maryland Hall for the Creative Arts, the city’s premier arts center. Galleries brim with rotating works from regional artists, and the stately halls buzz with workshops, performances, and community classes. Smaller gems like the Historic Annapolis Museum & Store on Main Street offer an intimate glimpse into colonial life and local lore, cleverly blending historical artifacts with unique gifts and books.
Insider tip: “The Naval Academy Museum is free and open to the public, but bring a photo ID for entry to the Academy grounds,” says docent Carol F.
Outdoor Adventures in Annapolis
When it comes to active things to do in Annapolis, the city’s natural beauty and waterfront setting offer endless opportunities for outdoor fun. Annapolis is world-renowned as America’s Sailing Capital, so hop aboard a classic sailboat with Schooner Woodwind Sailing Cruises for an unforgettable voyage across the Chesapeake Bay. The Woodwind’s tall masts and billowing white sails capture the spirit of nautical Annapolis, and the knowledgeable crew loves to share sailing tips and local lore as you glide past the Naval Academy.
Kayakers and paddleboarders flock to Annapolis Canoe & Kayak, where you can rent gear and launch from Spa Creek or nearby Quiet Waters Park. The meandering creeks are perfect for spotting herons, ospreys, and the occasional curious river otter. For those who prefer dry land, Quiet Waters Park is a local treasure. With miles of paved trails, shaded picnic spots, and a sun-drenched dog beach, it’s ideal for biking, rollerblading, or just soaking up the sunshine. In winter, the park’s outdoor ice rink becomes a favorite gathering place.
Want to combine exercise with sightseeing? Take a guided walking tour with Annapolis Tours by Watermark, where enthusiastic guides lead you through centuries-old streets, hidden gardens, and the stately Maryland State House. For runners, the Annapolis waterfront and historic district offer some of the most scenic routes in Maryland, with breathtaking views at every turn.
Fishing enthusiasts will find plenty of things to do in Annapolis as well. Book a charter with South River Boat Rentals and cast your line for rockfish, bluefish, and croaker, or just relax with friends while cruising the tributaries. Birdwatchers can visit the Smithsonian Environmental Research Center just south of town, where over 2,650 acres of research forests, wetlands, and trails await explorers.
Tip from an Annapolis regular: “The sunset sailing cruises on the Woodwind are pure magic—bring a jacket and your camera!” shares visitor Emily T.
Must-See Tours & Attractions
Among the most unforgettable things to do in Annapolis are the city’s legendary tours and iconic attractions. Step back in time at the Maryland State House, America’s oldest state capitol still in legislative use and the only one ever to have served as the nation’s capital. Roam its historic chambers, gaze up at the elegant dome, and imagine George Washington resigning his commission here in 1783—a moment etched into the nation’s memory.
The William Paca House & Garden, a National Historic Landmark, invites you into the world of a colonial Maryland governor. The meticulously restored 18th-century mansion is surrounded by two acres of lush, terraced gardens filled with boxwoods, heirloom roses, and tranquil ponds, offering a peaceful escape in the heart of downtown Annapolis.
For those eager to see Annapolis from the water, the Watermark Cruises and Tours fleet offers narrated boat tours, pirate adventures for kids, and romantic twilight cruises. Glide along the Severn River or Chesapeake Bay while learning about Annapolis’ pivotal role in American history. If you prefer to stay on land, hop aboard the Discover Annapolis Trolley Tours for a rolling adventure through historic neighborhoods, stately mansions, and vibrant shopping districts.
Quirky and unique attractions also pepper the things to do in Annapolis. The Kunta Kinte-Alex Haley Memorial at City Dock honors the legacy of the author of “Roots” and the millions of enslaved Africans who entered America at this port. Nearby, the St. Anne’s Church beckons with its striking stained glass and centuries-old graveyard, while the Hammond-Harwood House is an architectural masterpiece with guided tours and a fascinating collection of American decorative arts.
For families, the Pirate Adventures on the Chesapeake is a swashbuckling hit, where kids don pirate hats, hunt treasure, and fire water cannons on a real “pirate ship.” Meanwhile, the United States Sailboat Show each October transforms City Dock into a sea of gleaming masts and gleeful sailors.
Insider tip: “Don’t miss the Paca House gardens in late spring—the azaleas are jaw-dropping!” says local gardener Denise L.
Festivals & Events You Can’t Miss
The vibrant festival scene is one of the most exhilarating things to do in Annapolis, with events lighting up the calendar year-round. Kicking off in April, the Annapolis Film Festival brings independent filmmakers and movie fans together for four days of riveting screenings, panels, and parties across historic downtown cinemas. It’s a chance to mingle with directors, discover new favorites, and soak up creative energy.
Spring and fall see the city’s most iconic gatherings: the Annapolis Spring Sailboat Show and the legendary United States Sailboat Show, drawing maritime enthusiasts from around the globe. City Dock erupts with colorful sails, live music, and nautical vendors, while test sails and on-board tours let you channel your inner skipper.
For a taste of local flavor, the Maryland Seafood Festival each September is a can’t-miss event. Held at Sandy Point State Park, it’s a rollicking celebration of crab soup, oyster shucking, live music, and family fun—all with panoramic Bay Bridge views. Foodies will also love the Annapolis Restaurant Week, when dozens of restaurants offer special prix fixe menus, and the Chocolate Binge Festival in December, where artisan chocolatiers, holiday lights, and sweet treats transform West Street into a wonderland.
The city’s patriotic spirit bursts forth each July at the Annapolis Fourth of July Parade & Fireworks, with marching bands and dazzling pyrotechnics lighting up the harbor. In December, the Eastport Yacht Club Lights Parade turns the waterfront into a twinkling scene straight out of a storybook, as festively decorated boats cruise the chilly waters.
Things to do in Annapolis for music lovers include the long-running Annapolis Blues Festival at Sandy Point, where legendary performers jam against a backdrop of sand and sails. Culture seekers will appreciate the Kunta Kinte Heritage Festival each September, a joyous tribute to African and African American culture with drumming, dance, and soul food.
Insider tip: “Bring a picnic blanket and get to the City Dock early for the best fireworks viewing on the Fourth!” recommends festival-goer Alex D.
Music & Nightlife Hotspots
As the sun sets over the Chesapeake, things to do in Annapolis shift into high gear with a nightlife scene that’s surprisingly eclectic for a city of this size. Let’s start with the legendary Rams Head On Stage, a nationally acclaimed music venue hosting everything from Grammy winners to up-and-coming indie bands. The intimate setting—just 300 seats—means every show feels like a private concert, and the sound system is second to none. Grab dinner at the adjoining Rams Head Tavern before catching a show.
For a more casual vibe, locals flock to Reynolds Tavern, where the cellar-level 1747 Pub serves up craft beers, hearty fare, and raucous live music in a candlelit colonial setting. Across Main Street, Middleton Tavern mixes Chesapeake seafood with live pianists and jazz, while Dock Street Bar & Grill pulses with late-night revelers, spontaneous dance parties, and legendary burgers.
If craft cocktails are your thing, Sailor Oyster Bar shakes up inventive drinks alongside some of the city’s freshest oysters, all in a sleek, ship-inspired hideaway. Beer lovers can hop from Forward Brewing to Annapolis Market House for unique local pours and vibrant people-watching.
Don’t overlook the city’s love for open-air nightlife. In summer, the Boatyard Bar & Grill in Eastport becomes the place to soak up live music, cold drinks, and delicious fish tacos on its lively patio. Meanwhile, the Metropolitan Kitchen & Lounge on West Street hosts rooftop DJ sets and jam sessions that keep the good vibes going late into the night.
Tip from a night owl: “Rams Head On Stage books phenomenal acts—buy tickets early because shows almost always sell out!” advises music fan Brandon R.
Where to Shop in Annapolis
Shopping is one of the most charming things to do in Annapolis, blending indie boutiques, high-end galleries, and quirky shops with the city’s historic character. Strolling down Main Street, you’ll encounter everything from nautical outfitters to elegant jewelry stores, all housed in lovingly preserved 18th- and 19th-century storefronts.
A must-visit is Hatton Regester Green Jewelers, where gemologists craft bespoke pieces inspired by the colors of the bay. Across the street, The Annapolis Bookstore is a bibliophile’s dream, with well-curated shelves, cozy nooks, and regular author events. Mills Fine Wine & Spirits provides expert recommendations for every palate, while Art Things supplies creative souls with every imaginable paint, brush, and sketchbook.
If you’re seeking nautical flair, Helly Hansen Annapolis offers rugged-chic rain jackets, sailing gear, and classic stripes perfect for a day on the water. The Annapolis Pottery showcases hand-thrown ceramics with Maryland motifs, ideal for bringing a touch of Chesapeake charm back home.
On West Street, the Annapolis Arts District buzzes with galleries like McBride Gallery and FinArt Gallery & Studios, where you can meet artists at work and take home one-of-a-kind paintings or sculpture. Farmers’ markets such as the Anne Arundel County Farmers’ Market beckon on weekends with fresh produce, flowers, and artisanal treats.
Things to do in Annapolis for antique lovers include browsing the treasure troves at Peabody Fine Art & Antiques and Zachary’s Jewelers, where history and craftsmanship collide.
Insider tip: “Parking can be tight downtown—try the Knighton Garage and walk up Main Street for the full shopping experience,” suggests shop owner Sarah M.
Local Sports & Stadium Experiences
For sports fans, there are few things to do in Annapolis more thrilling than catching a game or cheering on the Midshipmen at Navy-Marine Corps Memorial Stadium. Home to the Navy Football and Navy Lacrosse teams, this state-of-the-art stadium is a living tribute to America’s armed forces, and game days here are legendary. The pre-game tailgates are exuberant, the flyovers awe-inspiring, and the crowds passionate. Don your blue and gold, belt out “Anchors Aweigh,” and feel the stadium pulse with tradition.
Lacrosse is practically a religion in Maryland, and the annual NCAA Men’s Lacrosse Championship is frequently hosted at the stadium, drawing fans from across the country. Soccer aficionados can catch the new Maryland Bobcats FC or enjoy the up-and-coming Annapolis Blues FC of the NPSL, who play their home matches at Navy-Marine Corps Memorial Stadium and ignite the stands with energy and local pride.
Boating is as much a sport as a way of life in Annapolis. Every Wednesday night from April through September, Eastport’s Annapolis Yacht Club hosts the Wednesday Night Races, when dozens of sailboats compete right in Spa Creek, their colorful spinnakers billowing against the sunset. Watching from City Dock, the Eastport Bridge, or a waterside restaurant is a beloved local tradition.
Marathoners and cyclists will find things to do in Annapolis year-round, with events like the Annapolis Running Classic and Lifeline 100 Century Ride drawing athletes of all stripes.
Tip from a sports fanatic: “Arrive early for Navy football games—the Brigade March-On is a sight you’ll never forget!” says season ticket holder Mike J.
Theatre & Performing Arts in Annapolis
For culture lovers, the performing arts are among the most rewarding things to do in Annapolis. The city’s thriving theatre scene is anchored by Maryland Hall, a stately arts center that hosts everything from symphony orchestras and ballet to jazz concerts and Broadway musicals. The grand main theater shimmers with energy on performance nights, while intimate studios upstairs host recitals, gallery talks, and dance classes.
Colonial Players of Annapolis is a community theatre icon, delighting audiences since 1949 with classic plays, contemporary works, and a devotion to local talent. The cozy theater-in-the-round puts you right in the heart of the action, and their imaginative sets and performances often earn rave reviews.
On West Street, the Annapolis Shakespeare Company brings the Bard to life with inventive stagings, period costumes, and candlelit ambiance. Their productions range from Shakespearean classics to lively cabarets, and the company’s dedication to craft is evident in every line.
Dance fans should check the schedule at Ballet Theatre of Maryland, Maryland’s premier professional ballet company, for stunning performances that span beloved fairy tales to bold, modern choreography. The Live Arts Maryland choral and orchestral performances, held at the Maryland Hall and St. Anne’s Church, transport audiences with moving renditions of everything from Mozart to modern pop.
Things to do in Annapolis for families include catching a show at the Compass Rose Theater, known for its innovative children’s productions and educational programs.
Insider tip: “Check out the Sunday matinees at Colonial Players—they’re a steal, and you’ll often get to chat with cast members after the show,” shares theater-goer Lila N.
In every season, Annapolis sparkles with a diversity of things to do that blend the old and new, the adventurous and the serene. Let this city’s charm, flavor, and vibrant spirit sweep you up—there’s always a new adventure waiting around the next cobblestone corner.
