As the capital of Maryland, Annapolis is a city that effortlessly blends its rich history with modern-day attractions. Nestled on the shores of the Chesapeake Bay, this charming city offers something for everyone, from history buffs and art enthusiasts to outdoor adventurers and food lovers. Its small, walkable historic district is perfect for exploring on foot, while the surrounding areas feature more expansive shopping centers, picturesque parks, and vibrant communities.
Whether you’re a local or a visitor, there’s no shortage of exciting things to do in Annapolis.
Dive into History
Annapolis is a city where history comes alive. As one of the oldest cities in the United States, it has preserved much of its colonial charm. Start your journey at the Maryland State House, the oldest state capitol in continuous legislative use. This historic landmark played a pivotal role in American history, serving as the site where George Washington resigned his commission as commander of the Continental Army in 1783.
For a deeper dive into the past, visit the William Paca House and Garden, a beautifully restored Georgian mansion that once belonged to one of the signers of the Declaration of Independence. The adjacent gardens offer a peaceful retreat and a glimpse into 18th-century horticulture.
\History enthusiasts should also explore the James Brice House, another architectural gem from the colonial era, and the Banneker-Douglass Museum, which celebrates African American history and culture in Maryland. This museum provides an insightful perspective on the state’s diverse heritage, blending historical narratives with contemporary art exhibits.
Learn About Maritime Heritage
Given its location on the Chesapeake Bay, Annapolis has a strong maritime tradition. The Annapolis Maritime Museum is the perfect place to learn about the region’s seafaring history and the ecological importance of the bay. Admission is free, and the museum frequently hosts engaging events and educational programming.
No visit to Annapolis would be complete without a stop at the United States Naval Academy. This prestigious institution has been training officers for the U.S. Navy and Marine Corps since 1845. Visitors can take a guided tour of the campus, where they’ll learn about its storied history, see impressive monuments, and visit the Naval Academy Museum, which showcases artifacts like historic flags and naval equipment.
Experience Arts and Culture
Annapolis boasts a thriving arts and culture scene that rivals larger cities. From May to November, the First Sunday Arts Festival transforms the city into a bustling hub of creativity. Musicians, craft vendors, and fine art dealers gather downtown, offering a lively experience for visitors.
Throughout the year, you can explore local galleries such as the McBride Gallery, which showcases works by regional and national artists. Music lovers should check out the Annapolis Symphony Orchestra, known for its outstanding performances at Maryland Hall. Whether you prefer classical concerts, contemporary art, or live theater, Annapolis offers an abundance of cultural experiences.
Get on the Water
Annapolis is often called the Sailing Capital of the United States, and for good reason. The Chesapeake Bay is a sailor’s paradise, and plenty of ways exist to get out on the water. Watermark Cruises offers scenic boat tours of the bay, providing a relaxing way to enjoy the city’s beauty from the water. If you feel more adventurous, consider joining a Schooner Woodwind Sailing Cruise. These 74-foot sailboats offer a variety of tours, including sunset sails and themed outings.
For those with their own boats, Annapolis features several marinas where you can dock or launch. Even if you’re not hitting the water, simply spending time at the City Dock is a delightful experience. This bustling area offers stunning views, vibrant shops, and a front-row seat to the city’s maritime culture.
Savor the Culinary Scene
Annapolis’s culinary offerings are as diverse as its attractions. Fresh seafood is a staple, with many restaurants serving Chesapeake Bay specialties like crab cakes, oysters, and rockfish. Carrol’s Creek Cafe and Cantler’s Riverside Inn are popular spots for waterfront dining with fresh, locally sourced seafood.
In the historic district, you’ll find a mix of cozy cafes, gourmet restaurants, and lively pubs. Whether you’re looking for an elegant dinner or a casual bite, Annapolis has plenty of options to satisfy your cravings. Don’t forget to explore the city’s craft beer and wine scene, with local breweries and vineyards offering tastings and tours.
Discover Unique Shopping
Shopping in Annapolis is an experience in itself. The city’s historic district is lined with boutique shops offering everything from handmade jewelry to nautical-themed gifts. For more extensive retail therapy, head to Westfield Annapolis Mall, which features a mix of high-end stores and popular chains.
Antique enthusiasts will enjoy browsing the quaint shops in Maryland Avenue and State Circle, where you can find vintage treasures and one-of-a-kind items. Whether you’re searching for a unique souvenir or the perfect gift, Annapolis’s shopping scene has something for everyone.
Experience Seasonal Events
Annapolis’s calendar is packed with exciting events throughout the year. The Annapolis Film Festival in spring showcases independent films and brings together filmmakers and cinephiles. Summer is a great time to enjoy outdoor concerts and festivals, while fall offers the Maryland Renaissance Festival, a family-friendly event filled with period costumes, jousting, and traditional fare.
During the holiday season, Annapolis transforms into a winter wonderland. The Eastport Yacht Club Lights Parade is a local favorite, with boats decked out in dazzling lights cruising through the harbor. The city’s festive atmosphere, combined with its historic charm, makes it a magical destination for holiday celebrations.
55+ Communities in Annapolis
Heritage Harbour
High $200s – Low $800s
Residents of Heritage Harbour don’t need to leave their community to get out on the water. The amenities of this large community of 1,600 homes include a boat dock, boat storage, a pier, and boat launch.
This community provides residents with the experience that many people want living in or near Annapolis. Homes are just minutes from the center of the city, but the woods and views of the water offer a peaceful place to call home.
The active adult community includes condos, attached, and single-family homes that vary widely in size and price, offering plenty of options for various budgets.
Four Seasons at Saint Margaret’s
High $400s – Low $500s
Located across the Severn River on the north side of Annapolis, Four Seasons at Saint Margaret’s is a condo community with 166 homes offered for resale.
The community’s amenities include a clubhouse with lounge, meeting rooms, a billiards room, and card room. Outside, residents can enjoy the outdoor pool and patio, or the wooded surroundings of this quiet neighborhood. Within minutes, residents can walk to parks and the waterfront.
Element at Mill Creek
High $400s – High $600s
An up-and-coming 55+ community, Element at Mill Creek will have 140 condos upon completion. The community also offers amenities such as a state-of-the-art fitness center, a social lounge, and pickleball courts.
Construction began in 2022, and the planned condo homes will range from 1,076 to 1,853 square feet with one to three bedrooms, two or two-and-a-half bathrooms, and outdoor parking. Also, the community’s location is within 15 minutes of Downtown Annapolis and 45 minutes of Baltimore.
Why Visit or Live in Annapolis?
Whether you’re planning a weekend getaway or looking for a new place to call home, Annapolis offers a unique blend of history, culture, and natural beauty. Its walkable historic district, vibrant waterfront, and diverse attractions make it a standout destination in Maryland.
From exploring centuries-old landmarks to sailing the Chesapeake Bay, there’s no shortage of things to do in Annapolis. So whether you’re visiting for the first time or considering a move, Annapolis invites you to experience all it has to offer.
