MoneyINC Logo
Years of

The 20 Best Things to do in Annapolis for First Timers

St. Anne's Church

As befits the "Sailing Capital of the U.S.", Annapolis is loaded with maritime heritage. If you’ve even the vaguest interest in naval history, you’ll find no shortage of things to see and do in Maryland’s capital. But the fun doesn’t end there. From parks to memorials, beaches to shopping malls, Annapolis has it all. Whether you’re traveling on business or on leisure, alone or with the family, don’t miss checking out a few of these tried and tested Annapolis highlights.

Annapolis Maritime Museum & Park

20. Annapolis Maritime Museum & Park

Annapolis has a rich naval tradition, something that’s more than apparent at the small but exquisitely welcoming Annapolis Maritime Museum & Park. Housed on the premises of the historic McNasby Oyster Company, the museum offers a smorgasbord of engaging exhibits, environmental programs, camps, and community events throughout the year. The views over the Chesapeake Bay and the adjacent beachside park (which comes complete with a very worthwhile wooden boat exhibit), meanwhile, are worth the visit alone.

Westfield Annapolis Mall

19. Westfield Annapolis Mall

If you’re hankering after some retail therapy, you’ll find few better places to indulge your spending habit than at the Westfield Annapolis Mall. Ever since it first opened its doors in the 1980s, Westfield has served as the city’s primary shopping destination. According to those in the know, the vast site can get a little tiring on the feet, so be sure to wear your comfiest shoes before heading off. The shops on offer are a good mix of chains and boutiques, while the outstanding variety of restaurants and cafes will make sure you don’t go hungry. There’s even a movie theatre if you feel like taking in a flick during your visit.

Thomas Point Shoal Lighthouse

18. Thomas Point Shoal Lighthouse

Built in 1875, the Thomas Point Shoal Lighthouse is the last remaining screw-pile lighthouse to still operate from its original location. Now a National Historic Landmark, the lighthouse welcomes visitors on most Saturdays during the season (June until October). With trained docents on hand to talk you through the significance of the lighthouse in Maryland’s rich naval history, it’s more than worth the 30 - minute boat ride to get there (although those who forgot to pack their sea legs might want to make sure they time their visit according to the weather).

St. Mary’s Church

17. St. Mary’s Church

Whether you’re an atheist, a Christian, or plain undecided, St Mary’s Church is well worth a visit. Located on the former property of Charles Carroll Carrollton, the only Catholic signer of the Declaration of Independence, the church is as magnificent today as it was when it was first built. The stained-glass windows are a sight to behold, while the scale and detail of the architecture is spellbinding. As the church still holds regular services, it’s worth checking the website beforehand so you can time your visit accordingly.

Maryland World War II Memorial

16. Maryland World War II Memorial

The Maryland World War II Memorial is a moving tribute to the generation of men and women who fought for their country in the second world war. Located an easy 5-minute drive from Historic Annapolis, the memorial bears a list of Maryland residents who died in battle, together with a series of plaques marking the timeline of the war. Quiet, peaceful, and offering breathtaking views over the Severn River and Naval Academy, it’s a must-do for all first-time visitors to Annapolis.

Great Frogs Winery

15. Great Frogs Winery

If all the sightseeing has left you with a thirst, a quick pit stop at Great Frogs Winery could be just the thing to revive you. The rustic, artisan winery is a great place to sample a superb collection of award-winning local wines, not to mention an equally fabulous selection of local cheeses, olives, and wine crackers. The service is beyond hospitable, while the relaxed, welcoming ambiance goes down just as nicely as the wines.

B&A Trail

14. B&A Trail

Walk it, bike it, or jog it… however you care to traverse it, the B&A Trail is a must-do for nature lovers. Well maintained and lined with plenty of trees for shade, it’s a great way to explore the area. Thanks to its straight, easy paths, even those of questionable fitness should be able to manage the trail without any problems… although if you can’t quite manage the entire length without a few pitstops, you’ll find plenty of benches and even a few coffee shops pitted along the way.

Chesapeake Bay Bridge

13. Chesapeake Bay Bridge

No visit to Annapolis is complete without at least one visit to Chesapeake Bay Bridge. The historic landmark offers some of the best views of the bay you’ll find anywhere in the city, and while traffic can get a little congested in the summer months, it’s still more than worth the effort. Just be warned that due to the height of the bridge, you might experience some mild ‘rocking’ in windier weather.

Sandy Point State Park

12. Sandy Point State Park

In June 1952, Sandy Point State Park opened its gates to its first visitors. Nearly 70 years later, it’s still one of Annapolis’s best destinations for all-round family fun. Located along the northwestern shore of Chesapeake Bay, the park comprises of 786-acres of beaches, picnic areas, trails, and stunning water views. The range of amenities and activities on offer is faultless, with as many opportunities for fishing, crabbing, boating, swimming, hiking, and wildlife watching as you could dream of.

The Kunta Kinte - Alex Haley Memorial

11. The Kunta Kinte - Alex Haley Memorial

As landmarks go, you’ll find few in Annapolis quite so affecting as the Kunta Kinte - Alex Haley Memorial… nor many that have a better position. Set smack bang in the heart of Annapolis, it’s a great place to sit with some takeout in the evening and soak up some local flavor. If you’re lucky enough to visit in September, you might even catch the Annual Kunta Kinte Heritage Festival, a fun-packed event with enough arts & crafts, food, local entertainment, and activities to keep the whole family happy.

Pennsylvania Dutch Farmer's Market

10. Pennsylvania Dutch Farmer's Market

For a true taste of Annapolis, head straight to the Pennsylvania Dutch Farmer's Market. Loaded with every type of Amish delicacy you can imagine (pretzel dogs, donuts, candy, cheesecakes, pies, homemade snacks, cakes, root beer, breads, smoked and cured meats, sticky buns, fried chicken, cinnamon rolls… the list goes on), it’s the perfect place to forget the diet and get stuck into some truly scrumptious food.

William Paca House & Garden

9. William Paca House & Garden

Built by former Governor of Maryland William Paca in the 18th century, William Paca House & Garden makes a superbly pleasant way to while away a few hours. Take a tour of the outstandingly well-preserved building before taking a stroll in the equally well-maintained grounds. Splendid though the house and grounds are, the chief attraction (according to past visitors, at least) is the incredibly friendly staff and guides, who are more than willing to answer as many questions on the history and significance of the house as you can throw at them.

St. Anne's Church

8. St. Anne's Church

Like many of Annapolis’s finest sights, St. Anne's Church has a rich history dating all the way back to the 1700s. Originally built in 1704, the church’s congregation quickly grew to such numbers that in 1775, the premises were razed to the ground to make way for a bigger building. After the Revolutionary War delayed construction, the new church was eventually completed in 1792, only to be destroyed by fire 60 years later. Within a year of the fire, the church was restored to its former glory, and it’s that final building that still stands today. A masterpiece of stained glass and 19th-century architecture, it’s well worth a few hours of anyone’s time.

Hammond-Harwood House

7. Hammond-Harwood House

Hammond-Harwood House (or the "jewel of Annapolis", as it prefers to call itself), is an architectural beauty. Built by William Buckland in the late 18th century, the building is a hymn to Anglo-Palladian style, while the impressive array of exhibits chronicling the lives and times of the house’s past occupants is fascinating. To get the full experience, a guided tour comes highly recommended. Throughout the year, the house hosts regular special tours, talks, lectures, and family programs, so be sure to check the website before visiting to see what’s happening.

Maryland State House

6. Maryland State House

The beautifully restored Maryland State House is a must for history buffs. Even if you thought you already knew all there was to know about George Washington, we guarantee you’ll come away from a tour with a few more facts up your sleeve. Granted, the building is on the small side, but there’s enough to see and do to justify at least a few hours of your time.

Ego Alley

5. Ego Alley

Come dusk, you’ll find few better spots in Annapolis than Ego Alley, a narrow waterway that boasts an impressive parade of luxury liners every evening. Grab an ice cream from the fabulous Storm Brothers Ice Cream Factory before parking yourself on a bench to soak up the sights. Once you’ve absorbed just as much of Annapolis’s maritime heritage as you can take, you’ll find any number of great restaurants in the area to get your fill of local cuisine.

Quiet Waters Park

4. Quiet Waters Park

If you’re looking to soak up some nature away from the buzz of the city, you’re unlikely to find many places better suited to it than Quiet Waters Park. Set over an expansive 340 acres, the park boasts everything from a sculpture gallery and garden to a playground, bike trails, formal gardens, wooded trails, picnic areas, and more besides. In the summer months, there’s the chance to rent a canoe or kayak and brave the lakes (or if you’re lucky, even take in an outdoor concert) while in the winter months, a giant ice rink appears as though by magic. Just be aware the park is closed on Tuesdays.

Banneker-Douglass Museum

3. Banneker-Douglass Museum

The Banneker-Douglass Museum might not be the biggest museum around, but you’ll find few quite so loaded with history. Set in the former Mount Moriah African Methodist Episcopal Church, the museum does a fine job of telling the story of African American heritage through a series of highly engaging, thought-provoking exhibits, programs, and projects. Open Tuesday through Saturday from 10 a.m. to 4 p.m., the museum offers free admission to all.

Historic Annapolis

2. Historic Annapolis

No trip to Annapolis is complete without a visit to Historic Annapolis. The area, which extends from a series of row houses in Main Street all the way to the harbor and downtown, is replete with history and intrigue, from the cute little houses with their paintbox colored doors to the cobbled streets and scores of shops, restaurants, and curiosities. Whether it's for lunch, shopping, or a memorable photo opportunity, the district is an all-round crowd-pleaser.

United States Naval Academy

1. United States Naval Academy

Even if it wasn’t for the must-see sight of the ‘noon meal formation’, the United States Naval Academy would be worth the trip for the beautiful campus alone. Take a guided walk ($10.50 per adult; $9.50 for seniors and $8.50 for children) of the campus for the lowdown on the stunning Beaux-Arts architecture and landscaping, not to mention a fascinating insight into Maryland’s naval history. Just be aware that opening hours vary by season: between March and December, the Academy opens from 9 a.m. to 5 p.m daily. In January and February, the opening hours are Monday – Friday, 9 a.m. - 4 p.m., and on Saturdays and Sundays, 9 a.m. to 5 p.m.

Liz Flynn

Written by Liz Flynn

Liz Flynn has worked as a full-time writer since 2010 after leaving a career in education. She finds almost all topics she writes about interesting, but her favorite subjects are travel and food. Liz loves the process of researching information, learning new things, and putting into words what others who share her interests might like to read. Although she spends most of her time writing, she also enjoys spending time with her husband and four children, watching films, cooking, dining out, reading, motorsports, gaming, and walking along the beach next to her house with her dog.

Read more posts by Liz Flynn

Related Articles

Stay ahead of the curve with our most recent guides and articles on , freshly curated by our diligent editorial team for your immediate perusal.
As featured on:

Wealth Insight!
Subscribe to our Exclusive Newsletter

Dive into the world of wealth and extravagance with Money Inc! Discover stock tips, businesses, luxury items, and travel experiences curated for the affluent observer.
linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram