Urban Dwelling

Sean Pavone/shutterstock.com
Sean Pavone/shutterstock.com


eat, drink and be merry
This Hip State Capital is More than Politicking and Boating.


“Annapolis is a drinking town with a boat problem,” jokes the friendly bartender manning the taps at BAROAK Cookhouse & Taproom (126 West St.). This beer-centric bistro is located inside the chic Loews Annapolis Hotel, and its curated selection of mostly Belgian beers has caught the attention of this wine-and-spirits-loving town. BAROAK is part of the state capital’s culinary renaissance, adding to the festive atmosphere that thrives in Annapolis year-round.

Annapolis boasts several new and notable eateries like Preserve Restaurant (164 Main St.), where two graduates of the CIA (not the spies—the Culinary Institute of America) showcase their talent for pickling, preserving and fermenting local produce. There’s also Vida Taco Bar (200 Main St.) spinning out Mexican street food in a hipster atmosphere. Pusser’s Caribbean Grille on City Dock is notorious for their Painkiller cocktails. It’s hard to beat the Southern hospitality found at Iron Rooster (12 Market Space), a waterfront restaurant serving breakfast all day—do not miss their homemade pop tarts.

Dave Newman/shutterstock.com
Dave Newman/shutterstock.com

Live music is an Annapolis tradition dating back to when Dr. Alexander Hamilton founded the Tuesday Club in 1745. Nineties rock band Good Charlotte got its start here. Students from two venerable colleges located in downtown Annapolis—the U.S. Naval Academy and St. John’s College—add a youthful buzz to the music scene. Ram’s Head On Stage (33 West St.) is the place to see a variety of performers in an intimate concert setting. This venue showcases singers, comedians and vintage cover bands.

Despite many cutting-edge attractions, Annapolis remains a town steeped in tradition. A collection of colonial-period houses stand side-by-side on the streets surrounding the magnificent Maryland State House (100 State Circle). You can see its wooden dome from nearly every corner in downtown Annapolis. Inside the rotunda flies a replica of a flag used by the 1783 Continental Congress when it met in the Old Senate Chamber. “During this time, George Washington officially resigned as Commander in Chief of the Continental Army, and the Treaty of Paris was ratified,” explains research historian Jean Russo. “The Maryland State House is the only statehouse ever to serve as the nation’s capitol.”

Courtesy of Preserve Restaurant
Courtesy of Preserve Restaurant

Though landlubbers have a lot to love, the pulse of the city beats at the Annapolis City Dock. Watch boats of all sizes—from dinghies to luxury yachts—motoring in so passengers can grab a snack from Sofi’s Crepes (1 Craig St.) or the Potato Valley Café (47 State Circle, Suite 100). Consider taking a cruise around the Chesapeake Bay yourself. Climb aboard The Harbor Queen or Miss Anne Riverboat; these ships offer 40-minute jaunts around the seaport and full-day roundtrip cruises to St. Michael’s. Annapolis Sailing offers two-hour cruises on their historic schooners.

Both Main Street and Maryland Avenue have multiple shops and galleries worth exploring. Some standouts: Re-Sails (42 Randall St.), with items made from yacht sails, and Dear Annie (65 Maryland Ave.), with affordable designer fashions. Check out Ekaa (68 Maryland Ave.), whose owner, Ritu Sundershan, sources tribal textiles from her native India to make handcrafted clothing and home decor. –RS



Loews Annapolis Hotel
Bright, nautically inspired, contemporary hotel a few blocks from City Dock and the Maryland State House.
126 West St.; $270-$350/weekend night

Historic Inns of Annapolis
Old-world luxury located in three historic hotels in the heart of downtown: The Maryland Inn, Governor Calvert House and Robert Johnson House.
58 State Circle; $170-$200/weekend night



Sean Pavone/shutterstock.com
Sean Pavone/shutterstock.com


getting down in dixie
Visit for the History and Culture, Stay for the Lifestyle and Recreation.


Shhhh, can you keep a secret? Richmond is awesome. This town has all the cultural benefits of a prosperous urban center, without the numbing traffic of its neighbor to the north. Richmond’s progressive policies on preservation and beautification have inspired young innovators to begin startups. Graduates of local colleges, like Virginia Commonwealth University and University of Richmond, are settling down here and benefitting from the affordable housing, abundant recreation and many free events.

Richmond’s charms were not lost on Americans throughout history. Author Edgar Allen Poe lived in Richmond for many years, and the Poe Museum (1914 E. Main St.) is located in Richmond’s oldest house—circa 1737. There’s a fine assembly of Poe’s personal items, as well as an “enchanted garden” inspired by his poetry.

Jon Bilous/shutterstock.com
Richmond Canal Walk (Jon Bilous/shutterstock.com)

Historians scrutinize the Civil War from multiple perspectives in Richmond’s American Civil War Center located at Historic Tredegar (500 Tredegar St.). The exhibits catalog events leading up to war, describe experiences of enslaved people and offer insights about the legacy the Civil War left behind in the South. Housed in Tredegar Iron Works, living history actors answer questions in the park surrounding these sites.

Consider booking accommodations in Historic Shockoe Slip (East Cary Street and Shockoe Street). This is a central location from which you can explore Richmond’s Canal Walk (200 Third St.) or take a ride on a Riverfront Canal Cruise (139 Virginia St.). Shockoe Slip’s cobblestone streets are just two blocks from the impressive Virginia State Capitol and Capitol Square (1000 Bank St.). This neighborhood can be boisterous at night, thanks to crowds partying at the Tobacco Company Restaurant (1201 E. Cary St.). Visit the eco-friendly Urban Farmhouse Market & Cafe (1217 E. Cary St.) for a nutritious, locally sourced breakfast or lunch.

 Courtesy of Triple Crossing Brewing Company
Courtesy of Triple Crossing Brewing Company

Richmond’s artists are showcased in dozens of galleries and edgy murals painted on downtown buildings. Visit the Arts District on Broad Street, where you’ll see original artwork in assorted mediums. “Entrepreneurs [like me] are using Richmond’s historic tax credits to transform abandoned storefronts into galleries and restaurants,” explains Anne Hart Chay, owner of the vibrant Visual Arts Studio (208 W. Broad St.). Rosewood Clothing Co. (16 W. Broad St.) is another irresistible collection that exemplifies this pioneering spirit. After shopping, stop in Tarrant’s Cafe (1 W. Broad St.) for authentic Southern cuisine or Triple Crossing Brewing Company (113 S. Foushee St.) to sample flights of homemade brews.

Two iconic Richmond experiences are found on the west side of town—the Virginia Museum of Fine Arts (200 N. Boulevard) and Carytown, aka “Richmond’s Mile of Style” (West Cary Street). Carytown shops are open during the day, while the VMFA has some evening hours. Richmond’s largest art museum is an architectural masterpiece with free admission. On occasional Thursday and Friday nights, the VMFA hosts live music and wine, and its terraced sculpture garden is a brilliant place to watch the sunset.

This September, Richmond hosts the UCI Road World Championship cycling races on courses that pass many local landmarks—it’s a festive time to visit, but Richmond is fun year-round. Just remember: Let’s keep this secret to ourselves. –RS



The Berkeley Hotel
Historic, restored boutique hotel in Shockoe Slip. Newly renovated. Ask for rooms on upper floor.
1200 E. Cary St.; $200-$250/weekend night

The One Bed & Breakfast
Located near Carytown in the Museum District, this historic all-suite, modernized mansion offers a sumptuous breakfast buffet.
1 N. Boulevard; $195/weekend night


← Back to Fall Getaways

(September 2015)