Walks Around Annapolis: In Town and Nearby

We have loved walking around Annapolis and the surrounding areas since we have moved but we have gained a new appreciation for all that Annapolis has to offer during the COVID-19 lockdown. Every day, we take a walk and try to vary our routine and destinations. So we share with you our best walks – all within a 30 minute drive or less from the Flag House Inn

But first a word from our sponsors: If you aren’t a guest with us, please have a look at our web site, we’d love to have you stay with us. Our rates include parking on site (other hotels ding you $29/night) and hot cooked breakfast ($20-30/day or more elsewhere – and it’s delicious – check out our Insta ).

Our location can’t be beat, we are across from Naval Academy gate 1 (main entrance) and 2 blocks to city dock! You can book direct with us, click here …. Plan ahead and book early for your next visit, we fill up fast….

Thanks for listening – on with the list:

In town

Main St – West St – Church Circle – State Circle – Maryland Ave – Prince George – King George – This is the core of Colonial Annapolis and downtown and all of this is more more than 3-4 blocks from the front door! Stroll the shops and restaurants, explore the colonial themed homes, visit the State House where George Washington resigned his commission… it’s the oldest state house in the country

Murray Hill – Acton Place – Pocket Parks – Bounded by Duke of Gloucester, West St and Spa Creek, this well kept neighborhood is full of stately homes and great vistas. Start from Flag House Inn, walk past City Dock, go up Green St (alongside Historic Annapolis & Hats in the Belfry) and enter into the residential streets along Market St, Charles and Conduit St. Wind your way around to Murray, Lafayette, Southgate and other streets… Many streets have a tiny park where the street dead ends into Spa Creek, the largest of which is Acton Park at the end of Conduit, Charles, West & Shaw

Eastport Stroll – The “Maritime Republic of Eastport” (Self styled independence statement and yellow flags :-)), previously home to boat building and seafood processing factories, is full of unique restored homes, many great restaurants facing Spa Creek, and just absolutely great for a longer walk. Walk to the other end of Eastport to Davis’ Pub, a classic neighborhood spot.

West Annapolis – this is a longer walk, it’s about a mile to get to the start. Walk up King George, turn left and the road will wind around to the entrance at Annapolis St …. Flamant restaurant (great farm to table) will be on your left. Take a right at Giddings, Melvin or Monterrey, and eventually you’ll see water views and stately homes.

The Naval Academy – This is the safest (no uneven bricks and few cars) and most scenic and historic walk of all! Pick up a map from the sitting room, bring an ID to get through security (note – During Coronavirus lockdown, we need to escort you on to the Yard) and you are off and away. We suggest an immediate right turn leaving the security check point, walk along harbor/ waterfront, to Triton Light (single most scenic view in Annapolis) along boat basin/Severn river , cut through to Bancroft Hall / Stribling walk, past Chapel and Herndon Monument , on to Museum and across wooden bridge over College Creek to Hospital Point and John McCain’s grave… Work your way back past Worden Field and out thru gate 3 or walk down officers row and out Gate 1….

View from Triton Point

Out of Town (driving distance one way)

Greenbury Point (10 min) – our favorite hike outside downtown Annapolis – see our blog – only negative is sometimes the park closes for military training – check status here. Increasingly popular, the the loop walk is ~2.5 mi and add on side trails to get to 4 miles easily… Several look out points along the way

Bird in nest in water, Chesapeake Bay Bridge in background

On a clear day, both the Ospreys and Bay Bridge are in sight from Greenbury Point

Quiet Waters Park (10 min) – Large county park, the perimeter trail covers 4 miles, but plenty of shorter hikes – See our blog – be sure to walk the South River overlook trail for a great view out to the Chesapeake Bay. They also have a kayak/canoe / bike rental along a quiet creek

Quiet Waters Park faces the South River and a creek

Quiet Waters Park has lovely vistas overlooking the South River

Baltimore & Annapolis (10 min) and BWI Trail (30 min) – see our blog for our bike ride on the B&A. If hiking, drive a bit further up Route 2 for an easier access to the trail (it’s 1/2 mile walk to trail head from lot nearest to Annapolis). The trail goes all the way to BWI, and then you can do a loop around BWI and back – a 40 mile distance all in…

Man and woman in active weawr jogging down a paved path among trees

Go for a walk or bike ride on the Baltimore & Annapolis trail

Thomas Point Park (20 min) – details here and hiker’s perspective here – It’s not much of a walk but what a great perspective on the Bay, you can look up the Bay to the Chesapeake Bay Bridge, straight out is the famous Thomas Point Lighthouse and down the Bay is the mouth of the South River, Kent Island and Tilghman Island… Picnic tables available, bring a folding chair. Always great when paired with a trip to Great Frogs winery

Sandy Point State Park (15 min) – A gem of a park that fronts the Bay Bridge – can go swimming or hiking – the park gets plenty busy so go early. There is a one mile beach for a nice walk . Get all info here

Waterworks Park – (10 min) This is a fascinating set of trails – we walked the first 4 mi RT from nearby Housely road but you can go at least 10 miles. Trails are nice and wide, can be busy on weekends and excellent for mountain biking too. Heavily wooded/shaded. Some of the trail borders the original city reservoir. Overview article here City overview web page Extended trail map

Waterworks trail map at Housely Rd trailhead – take a pic with your phone before starting

Beverly Triton Nature Park (25 min) – 370 acres, 5 miles of trails, undeveloped park with beaches right on the Bay. Go early in summer as it fills up… We went over on a sunny Sunday afternoon, the park closed by 130p. Many easy walking trails and a long wide open beach. Bring some chairs / blanket and make an afternoon out of it… more pics below… Web site hiker’s perspective