What To Do While Visiting Annapolis in 2020

Visiting Annapolis During the Pandemic

What do you do in Maryland’s capital when two of its major attractions, the Maryland State House and the U.S. Naval Academy, are closed to the public? Luckily for those of us who love Annapolis, during this pandemic, visitors may explore the city, dine outside, and find many pleasant, fun, and safe activities to fill their days. 

Annapolis visitors cannot resist walking to the water's edge at Ego Alley in downtown Annapolis. Photo by Bob Peterson

Downtown in the open air

It doesn’t matter whether you’re visiting for the first time or for the 100th: no Annapolis visit is complete without a stroll of the Historic District and City Dock. Since Colonial times, visitors to Annapolis have been drawn to the water. Today, we walk up and down Main Street toward the harbor, stop to take a selfie at the Kunta Kinte - Alex Haley Memorial on Ego Alley and read the plaques to learn about the history behind it. Relax on a park bench at the Susan C. Campbell Park and soak in the view of the city anchorage, the Severn River, and out into the Chesapeake.

Visitors enjoy sitting and taking selfies near the beloved Kunta Kinte- Alex Haley Memorial Statue in the heart of Annapolis. Photo courtesy of Visit Annapolis and Anne Arundel County

Those who enjoy quieter streets with fewer tourists should walk up to Maryland Avenue and State Circle and explore the shops, restaurants, and galleries. Among SpinSheet staffer favorites are Galway Bay Pub, Annebeth’s of Annapolis (for specialty foods, wine, gifts, and chocolate), and the Maryland Federation of Art Circle Gallery. You may not be able to enter the Maryland State House, but the attractive grounds include some benches for resting your travel-weary legs.

If you continue around State Circle to Church Circle and go around almost 180 degrees, you’ll find West Street, a hub of restaurants and shops. First Sunday Arts Festival, held the first Sunday of the month, has taken place successfully this summer, and organizers plan to host it through November (check with firstsundayarts.com to make sure it’s happening). There are no food trucks this year, and vendors are spaced out to ensure social distancing. Visitors follow mask-wearing guidelines and limit their numbers in tents.

Those who are not comfortable with the “festival” idea may visit the vendors online at firstsundayarts.com/virtualfestival.

The Boatyard Bar and Grill's crabcakes are ah-mazing and sailors are always willing to walk across the Eastport Bridge in the Maritime Republic of Eastport to try them.

Dining al fresco

During the pandemic, the City of Annapolis has greatly expanded its outdoor dining capabilities all over town by redirecting traffic, erecting safety barriers, and bringing in more tables and umbrellas. Find the details about Annapolis Recovery Zones at annapolis.gov. The short version is as follows:

Daily: Market Space (the area around Annapolis Market House), Lower Dock Street, Lower Main Street, Maryland Avenue, and Eastport have redirected traffic to create space for open café-style seating.

Wednesday, Thursday, Friday: Dinnertime road closures to expand outdoor seating in the Forest Drive Corridor (Wednesdays only), Upper Main Street, and West Street.

Saturday and Sunday: Expanded hours for lunch and dinnertime road closures for outdoor dining on Upper Main Street and the first block of West Street.

The Maritime Republic of Eastport

Emanating its own distinct boating vibe, Eastport, known to the locals as the Maritime Republic of Eastport aka The MRE, is worth strolling across the Eastport Bridge to discover. Check out the restaurants on Severn Avenue, but don’t forget to walk down Fourth Street to go to the new Forward Brewing. The Annapolis Maritime Museum’s indoor exhibits are closed, but you may still stop by the docks to see the fishermen and the beach and take a ride on the Skipjack Wilma Lee (amaritime.org).

Eastport Eats

Although we’re not all in the office at the same time these days, when we are at our Eastport headquarters, the SpinSheet team favors a number of nearby restaurants, all of which offer takeout as well as seated meals.

Boatyard Bar and Grill—Best crabcake in town, pint-sized drinks, pleasant outdoor tent area.

Bread and Butter Kitchen—Great daily specials and breakfast sandwich, several waterview tables, casual.

Davis’ Pub—The crab pretzel addiction is a thing, yummy burgers, outdoor dining with umbrellas.

Eastport Kitchen—Check out the monthly menu as well as the regular one, amazing food, outdoor dining.

Grump’s—really good sandwiches and breakfasts, outdoor seating.

Leeward Market—breakfast sandwiches and pizza, café tables outside.

Sunrise at City Dock Annapolis, next to one of the Annapolis Sailing and Waterfront Center's sandbaggers.

Walk on the wild side

The Eastport neighborhood is known for its Street End Parks at the end of most of the streets on the peninsula. These are mini-parks, some with benches, some good for launching kayaks or standup paddleboards, and are open to the public. To check them out, just wander over the Eastport Bridge from downtown Annapolis, take your first left on Severn Avenue, and start exploring. The park at the end of First Street (just past Eastport Yacht Club) offers a nice skyline view. A few SpinSheet staffers like to go standup paddleboarding with the folks from East of Maui Boardshop from the Horn Point Park at the end of Chesapeake Avenue.

It’s neither new, nor a secret, but we’re always surprised to hear Annapolis residents say they’ve never been to Quiet Waters Park, a wonderful public space with six miles of paved trails along Harness Creek and the South River, picnic and playground areas, a dog beach, kayak and SUP rentals, an outside concert venue, art gallery and gathering space, ice skating rink, and ample parking. It’s a 3.4-mile drive from downtown Annapolis and about as family friendly as it gets ($6 entry fee for cars; walk-ins free).

You drive 3.8 miles to go from Annapolis’s Historic District to the Ellen O. Moyer Back Creek Nature Park down Edgewood Road, a Mecca for maritime businesses and boats. There you will find wooden nature trails along Back Creek with signs about wildlife and conservation, the education center for Annapolis Maritime Museum, and a public kayak and SUP launch, where Capital SUP rents boards and gives lessons.

Sailors of all levels enjoy a two-hour sail or specialty cruise aboard the Woodwind Schooner. Photo courtesy of Facebook/schoonerwoodwind

Take a boat ride… of course

We at SpinSheet think the best way to visit Annapolis is by boat. Even if you’re only in town for a few hours, you have options for getting on the water.

Perhaps the fastest, easiest way to hop on a boat in Annapolis is taking Watermark’s Water Taxi. Find the taxi stop on City Dock. Touchless payment is available through the “Where in Annapolis” app.

We love Annapolis Electric Boat Rentals’s tagline for their Duffy electric boats: “Like a Tesla… but slower.” They offer one-, two-, and three-hour rentals, staring at $175.

Freshly refurbished and available for tours and cruises for the first time in 2020, the Skipjack Wilma Lee docks at and departs from the Annapolis Maritime Museum in Eastport.

Watermark Cruises has a number of tour boat offerings, the Harbor Queen departing from City Dock perhaps the most visible of them. They’re currently running at 50 percent or less capacity. All staff members wear masks, as do guests unless they’re eating or drinking.

No visit to Annapolis is complete without a sail on one of the Schooner Woodwind’s two beautiful 74-foot schooners located in America’s Sailing Capital. Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy, and cruises into the Chesapeake Bay. Schooner Woodwind offers a variety of specialty cruises throughout the year including: a lighthouse cruise October 3, where guests will sail past as many as three different lighthouses on the Chesapeake while learning about their history and importance from a guest lecturer from the Chesapeake chapter of the U.S. Lighthouse Society; and a cocktail cruise the evening of October 3 featuring appetizers, cocktails, wine, and beer while sun sets over the Chesapeake. Find the Woodwind and Woodwind II next to Pusser’s Caribbean Grille, and purchase tickets at schoonerwoodwind.com.

Catching a water taxi from City Dock is the quickest and easiest way to take a boatride in Annapolis. Photo courtesy of Watermark

If you prefer to be in charge, check out Chesapeake Boating Club in the Eastport neighborhood of Annapolis. Find the membership option that is right for you, and take the stress of boat maintenance, slip fees, and all the little costs associated with owning a boat out of the equation. The club has a fleet of east-to-sail J/80s and Harbor 20s, along cruising options such as J/32s, J105s, and a Benteau 331. Chesapeake Boating Club even offers learn to sail courses taught by J World Annapolis. J World offers certification from US Sailing and US Powerboating. Learn more at chesapeakeboatingclub.com.

Take a Walking Tour

In addition to cruises, Watermark also offers Walking Tours of Colonial Annapolis, including specialty tours such as an African American Heritage Tour and Historic Ghost Tour. Seeing a guide in Colonial garb wearing a face shield might seem strange, but hey, it’s a brave new world, and for Watermark, safety is paramount.

Visit Digitally

Although you cannot enter the capitol, find a Maryland State House 3D Tour.

The Historic Annapolis Museum Store may be closed, but you can shop online.

If you’re not comfortable visiting First Sunday Arts Festival in person, you may find the vendors online.

Find Annapolis events for sailors here.