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Undiscovered Baltimore

154 Things To Do In The 10 Neighborhoods You Need To Know About

If you talked to any Joe Schmo on the street about the best neighborhoods in Baltimore, they’d list the usual suspects: Canton, Federal Hill, Fells Point, Hampden. And while all of those are wonderful areas, and certainly popular for a reason, we wanted to feature some of the unheralded spots in our region. Many of these areas feel like the neglected step-children of their more popular counterparts, but there are plenty of reasons to celebrate these ’hoods on the rise— whether it’s affordable real estate, adorable mom-and-pop shops, undiscovered art scenes, or fantastic summer events.

As the weather gets warmer, it’s a great time to explore outdoor concerts, local parks, and summer festivals, whether as a visitor or future resident. We urge you to take a closer look at the Baltimore metro area because what you find might surprise you.

*Statistics from 2010 U.S. Census except where noted.


Population: 2,520 Median home price: $152,000 Own-to-rent ratio: 71.7 to 28.3 percent Miles from downtown Baltimore: 4.5*

Since the mid-’50s, Ashburton has been the home base for Baltimore’s African-American elite. It has produced generations of civic leaders including Mayor Stephanie Rawlings-Blake, who grew up in the neighborhood, and former Mayor Kurt Schmoke. Even one of Mayor Rawlings-Blake’s recent challengers, Catherine Pugh, calls the petite district north of Liberty Heights Avenue, east of Callaway Avenue, south of Sequoia Avenue, and west of Hilton Road, home. Full of older, well-kept homes on large lots with mature trees, Ashburton recalls parts of Cedarcroft or even Mt. Washington (though much less hilly). Nearby Lake Ashburton in Hanlon Park has a walking path around the reservoir that gets plenty of use while just a little farther down the road is Druid Hill Park, containing the Maryland Zoo in Baltimore and the Howard Peters Rawlings Conservatory and Botanic Gardens of Baltimore, which is named after Mayor Rawlings-Blake’s late dad, state Delegate Howard Peters “Pete” Rawlings, who died in 2003. Ashburtonites take their horticulture seriously, and the For-Win-Ash Garden Club (named for the communities of Forest Park, Windsor Hills, and Ashburton) is still very active. Every other year, it hosts a garden tour, but sadly, this is an off year. The recent renovation of Mondawmin Mall has given area retail a boost with a new Target, a Forever 21, and several other clothing stores, now open.


The Howard Peters Rawlings Conservatory offers weekly classes sure to please green thumbs. On May 5, learn how to create a succulent garden.

The Maryland’s Zoo’s Brew at the Zoo event—two days of craft and local beer sampling and live music—is May 26-27.

Get your engine running at the 2nd annual Druid Hill Auto and Motorcycle Extravaganza, August 25 from 9 a.m.-6 p.m.

Browse the offerings at the city’s newest farmers’ market every Wednesday evening from June through September at the Rawlings Conservatory.

Butchers Hill

Population: 1,889, Median home price: $250,000, Own-to-rent ratio: 51.1 to 48.9 percent, Miles from downtown Baltimore: 1.4

What used to be home to affluent German and Jewish butchers is now home to a diverse cross-section of the city. Butchers Hill is at the northwest end of Patterson Park, bounded by Fayette Street on the north, Patterson Park Avenue on the east, Pratt Street on the south, and Washington Street on the west. A mix of artists, Hopkins employees, students, and empty-nesters now reside in the neighborhood’s oversized brick row houses. Many of the wide, three-story houses are quite affordable for their size, making them attractive to rehabbers. One example of what can be done with these houses is Blue Door on Baltimore, a bed-and-breakfast that opened in 2007. The B&B offers a soothing experience for guests, many of whom are visiting because of nearby The Johns Hopkins Hospital. In fact, a main draw for Butchers Hill residents is its close proximity to Hopkins, Patterson Park, and Fells Point. But you don’t have to leave the confines of the neighborhood to experience urban culture, with places like neighborhood bar The Life of Reilly, which serves up authentic Irish cuisine. If something more upscale is your scene, there is Salt Tavern, which offers fare like duck-fat fries and Kobe-beef sliders in a modern setting. For a quick cup of coffee and a pastry, head over to Water for Chocolate. (Bonus: the shop’s iced drinks have coffee ice cubes so they don’t get watered down.) Then there is also, of course, the natural beauty of the city’s largest park right next door, with tennis and basketball courts, jogging and biking trails, and constant summer festivals.

Baltimore’s Backyard

While many houses surrounding the park don’t have big backyards, there is plenty of green space—–137 acres to be exact—–in adjacent Patterson Park. Here is just a sampling of things to do.

Splish Splash – The pool in Patterson Park is one of the city’s many great, affordable public pools. Pool season starts in June and runs through the last Sunday in August. There’s a lap pool, toddler water-play area, and adult swim times—–all for just $1.50 a visit.

Play Time – Although there are two playgrounds in the park, the one near Eastern Avenue between S. Milton and S. Montford Avenues may be the coolest in the city. Built in 2005, the playground pays tribute to city landmarks—–with row houses, a Bromo-Seltzer clock tower, and a gazebo that looks like the old park’s music pavilion.

Game On – Any athlete would feel at home, whether enjoying the park’s almost three miles of biking and walking trails, 10 tennis courts, four full-sized basketball courts, various multi-use fields, or the rink open for hockey in the winter and broomball in the summer.

Great Lake – Almost smack dab in the middle of the park is its boat lake, which is a combination of open water and wetland habitat for fish, waterfowl, and birds. The lake is great for fishing, wildlife viewing, or just an afternoon of feeding bread to the ducks.


Butchers Hill Flea Market and Craft Fair, located by the pagoda in Patterson Park, is the ultimate treasure trove for the bargain hunter. Tip: Get there early, as the seasoned residents of the neighborhood don’t sleep on this one. May 12, 9 a.m.-3 p.m.

PNC Concerts in Patterson Park run Tuesdays and Sundays throughout the summer. Grab a blanket and a picnic dinner while you listen to everything from salsa and reggae to bluegrass and funk. June 10 and 26; July 8, 17, 31; August 7 and 19, all at 6:30 p.m. (Rain dates are the following Wednesday.)

Latino Fest, one of many ethnic festivals celebrated in the park, is probably the most well attended. With authentic Latino music and delicious food, this annual outdoor party is a big draw for residents of all ethnicities. June 23, 12-10 p.m., and 24, 12-9 p.m. 


Population: 156 Median home price: $307,500 Own-to-rent ratio: 96.4 to 3.6 percent Miles from downtown Baltimore: 6.2

If you asked a 10-year-old to draw a picture of a storybook village, he or she would probably produce something closely resembling Dickeyville, a National Register Historic Preservation District on the western edge of Baltimore City. A cluster of 138 homes and buildings nestled along narrow, winding streets north of Windsor Mill Road, west of Wetherdsville Road, east of the city-county line, and south of Purnell Drive, Dickeyville got its start as a 19th-century mill village powered by the adjacent Gwynns Falls. Residents take extreme pride in preserving their nabe with not one but two governing bodies overseeing its architectural integrity. (White houses can only be repainted white; shutters are encouraged to be either black or dark green.) But all this enforced quaintness pays off with high home values and a close-knit community. The Dickeyville Garden Club, founded in 1940, hosts multiple community events throughout the year including a spring plant sale and autumn cook-off and bonfire. One of the best perks of living in Dickeyville is its proximity to Gwynns Falls-Leakin Park, a roughly 1,000-acre tract containing walking and biking trails, tennis courts, the Carrie Murray Nature Center, and Orianda House, a 19th-century Italianate mansion. There’s also the nearby 18-hole Forest Park Golf Course, with greens’ fees starting as low as $9.50.


This year’s Horticultural Society of Maryland’s Garden Tour will offer a peek behind the picturesque picket fences and stone walls of Dickeyville. June 3, 10 a.m.-4 p.m.

Dickeyville takes the Fourth of July seriously with a multiple-day celebration featuring a community dinner dance (June 30), brunch (July 1), and, of course, parade and picnic (July 4).

April through November, Friends of Gwynns Falls Leakin Park hosts Second Sunday in the Park, a day of free activities including guided hikes, tours of Orianda House, and free miniature train rides! 11 a.m.-3 p.m.


Population: 6,323 Median home price: $265,000 Own-to-rent ratio: 74.3 to 22.3 percent Miles from downtown Baltimore: 27.1

Hampstead is a Carroll County town just 30 miles northwest of Baltimore that seems straight out of another time. Main Street is reminiscent of quintessential small-town America, with an old-time police station and great antiquing. There are many sprawling farmhouses on Mt. Carmel Road and along Route 30, but also some beautiful Colonial houses built in the 1800s along Main Street. The central avenue of town also boasts quaint shops like Linens and Lace Tea Room, where you can find girls of all ages having tea parties, or independent floral shop Petals Flowers & Gifts. While there isn’t much for fine dining, there are certainly charming restaurants, like the 50-year-old Dean’s Restaurant, which feels like eating at your grandmother’s house with homemade desserts and delicious corn fritters. For a more casual atmosphere, there is Greenmount Station, known for its crab cakes and sports-bar atmosphere. And every great small town needs a diner, so Hampstead Diner is the spot where locals chow down on sausage gravy and chipped beef while they shoot the breeze about politics and gossip. For fresh produce, there is a farmers’ market at the fire station every Saturday starting on June 9. Plus, right in town, there’s a huge water park Cascade Lake, which is a six-acre, spring-fed lake with a roped-off area for swimming that includes various waterslides and platforms. For the history buffs, there’s a war memorial on Main Street and there are also several historic signs throughout the town marking different Civil War battles as people make their way up to Gettysburg, about an hour north.


Hampstead Day is a day to celebrate the town where they close off Main Street and feature nearly 150 vendors with kiddie rides, music, and food. May 19, 8 a.m.-4 p.m.

A Month of Sundays Summer Concert Series takes place in nearby Westminster City Park where, every Sunday in July, people bring their lawn chairs and picnic baskets to enjoy country, rockabilly, or Motown. Starting July 1, 6:45-9 p.m.

Hampstead Fire Company Carnival is a six-day event to celebrate the town’s volunteer fire company with a parade in their honor, as well as food, games, and entertainment. August 13-18, 6-11 p.m.


Population: 1,176 Median home price: $198,700 Own-to-rent ratio: 88 to 8.7 percent Miles from downtown Baltimore: 8*
*Statistics courtesy of Cummings & Co. Realtors.

Many people don’t even know how to pronounce this neighborhood (net-a-shawl), let alone know where it is. But, you probably drive by this Towson ’hood all the time since it’s located near Parkville, just west of Loch Raven Boulevard and south of Joppa Road. While it looks like a quintessential county suburb, the real estate is more affordable than its West Towson peers, but with all of the same space in its single-family homes. The ’40s and ’50s brick row homes are reminiscent of downtown architecture, but with the added bonus of front and backyards. Plus, shopping is a breeze with the walking-distance Towson Marketplace, which features stores like like Target, Marshalls, and Wal-Mart. There are plenty of local stalwarts within a stone’s throw, including Johnny Dee’s Lounge, which is a cavernous restaurant that pays tribute to the Colts and also has renowned shrimp salad. Just recently, there was some excitement when Gino’s Burgers opened right up the street, bringing the classic burger back to Baltimore. The cherished ’50-style Bel-Loc Diner and seafood haven Crackpot Restaurant are also close by. And don’t count out The Raven Inn, a dive bar beloved to the locals with entertaining bartenders and great deals on seafood. But a big part of the neighborhood demographic is families, who, most days, can be found enjoying the Pleasant Plains Elementary School playground. For even more space to roam, there is nearby Cromwell Valley Park, which boasts 380 acres of wetlands, meadows, gardens, and a farm right in the center of it, which is known for its organic methods. If organic is your thing, be sure to swing by the neighborhood’s farm stand on Putty Hill Avenue that runs every day in the spring, summer, and fall.


Towsontown Spring Festival is celebrating its 45th year and will feature four days of live music, beer gardens, carnival games, and countless vendors. May 3 (10 a.m.-3 p.m.), May 4 (5:30-9 p.m.), May 5 (10 a.m.-7 p.m.), and May 6 (1-7 p.m.).

Arts in the Park. This festival in Cromwell Valley Park showcases local fine artists, crafters, writers, and musicians. Also on hand are food, wine, and classic cars. May 12, 10 a.m.-5 p.m.; May 13, 12-5 p.m.

Fourth of July is a pretty big deal in this neighborhood. The fireworks at the former Luskins building are now put up right down the street. Residents can walk down to Pleasant Plains Elementary with chairs and picnic baskets to take in the view. July 4.


Population: 13,903 (combined), Median home price: $159,900 (Lauraville), $150,000 (Hamilton), Own-to-rent ratio: 73.5 to 26.5 percent (Lauraville), 48.6 to 51.4 percent (Hamilton), Miles from downtown Baltimore: 5.1

This hyphenated hamlet is really two neighborhoods tied together by the unifying thread of Harford Road’s business district, which starts in Lauraville just north of Argonne Drive and continues up through Hamilton to Northern Parkway. Quiet, tree-lined streets boasting a mix of bungalows, Foursquares, and farmhouses shoot off the main thoroughfare offering suburban ambiance within the city. Of course, these days, the area is probably best known for its many culinary hotspots (see sidebar). But the affordability of the neighborhood and its strong public and charter schools—–including Hamilton Elementary/Middle School, City Neighbors Hamilton, and City Neighbors High School—–also attracts many young families who can be found browsing the excellent selection of children’s books at Red Canoe Bookstore Café, playing in rec leagues at Herring Run Park, or biking around Lake Montebello. Parents can also enroll their budding thespians in classes at the Performance Workshop Theatre or drop off their tiny dancers at Mid-Atlantic Center for the Performing Arts, a ballet and contemporary dance studio. Mommy and daddy can have fun, too, at Charmed Life, an art gallery and tattoo parlor or at The Chop Shop, a hair salon with a 20-seat movie theater, which owner Lisa Hawks rents out for events. Downstairs from The Chop Shop is Blue Spark Barbershop, home of Bill the Barber, whose in-demand cuts start at $16. And just down the street is Beth’s DIY Workshop, where founder Beth Dellow provides space, tools, and training for do-it-yourselfers.

Destination Dining

If someone had said 10 years ago that Harford Road would become one of Baltimore’s hottest dining destinations, you would have laughed. But, now, you can eat your way from one end to the other. In fact, we recommend you do.

Fine Dining – The strip’s two highest-profile restaurants are Hamilton’s Clementine, which serves upscale comfort food and The Chameleon, which opened in Lauraville in 2001, way before Harford Road was cool.

Casual Dining – Enjoy the hefty crab cake at Koco’s Pub. The recently opened Tooloulou is favored for its Cajun cusine. Hamilton Tavern keeps ’em coming back with a seasonal menu of pub favorites. Los Amigos turns out traditional Mexican food. Big Bad Wolf’s House of Barbecue has excellent meats and sides. And the two local diners—–Lost in the 50’s and Valentino’s—–crank out classic eats, the latter 24/7.

Markets/Groceries – The Tuesday Market in Lauraville sells from June through October. Clementine’s chef/owner, Winston Blick, is opening Green Onion, a grocery which will sell Clementine prepared foods (such as their beloved charcuterie) and other comestibles. Get your daily bread at Hamilton Bakery.

Cafes – Lauraville is home to Zeke’s Coffee, which brews nearly 50 different roasts at its plant and sells them a few blocks away in a coffee shop. Try a cup with an award-winning muffin from Red Canoe Bookstore Café.


The Blue Water Berry Festival in Herring Run Park is a taste of summer with barbecue, music, vendors, and a native-dessert contest. June 23, 12-4 p.m.

The 19th Annual Hamilton Street Festival & Classic Car Show goes down July 28 and features a soapbox derby. 11 a.m.-7 p.m.

First Fridays offer visual and performing arts at galleries including Hamilton Arts Collective, Studio 55, and The Hamilton Gallery. Year-round.

Locust Point

Population: 2,138 Median home price: $292,500 Own-to-rent ratio: 70.8 to 29.2 percent Miles from downtown Baltimore: 2.7

Locust Point, the neighborhood once home to dock workers and their families, still has the industrial feel with its waterfront factories and Formstone houses. But, while the South Baltimore ’hood (with Lawrence Street to the west and the Patapsco River to the north, south, and east) held onto its blue-collar roots longer than its nearby compatriots, it also has new developments making it extremely attractive to homebuyers. Of course, there’s the behemoth condo complex Silo Point with its 360-degree views, swanky residences, and upscale restaurants. There’s also the Locust Point Dog Park on the corner of Latrobe Park, which has fancy amenities like Astroturf, rock features, and a doggie waterslide. And there is the former Tide Point campus, which just got bought by Fortune 500 company Under Armour, and features a waterfront boardwalk for jogging or yoga. Plus, there’s a free water taxi service on weekdays from the promenade over to Fells Point. And one of the newest establishments is shopping center McHenry Row, featuring the innovative Harris Teeter, where people from all over the city come to grocery shop. But you can’t ignore Locust Point standbys like the quaint, windowless J. Patrick’s Irish Pub, which features live Irish music multiple nights a week. There’s also the neighborhood bistro (and cleverly named) Hull Street Blues Café, which started as a saloon in 1889 and has a fantastic Sunday brunch. And don’t count out sports bar City Limits with its huge shuffleboard table and fresh-squeezed orange crushes. Also, if you want to get quite the waterfront vista (including the Under Armour and Domino Sugar signs), you should crack open some crabs on the roofdeck of L.P. Steamers. For the kids, there is spacious Latrobe Park with its tulip-lined pathways and large gated playground—–and they can cool off by visiting “Miss Twist,” who drives her turquoise ice-cream truck around the neighborhood delivering sweet treats. And lastly, while it’s no secret, the proximity to nearby Fort McHenry is an added bonus for any history buff.


Community Yard Sale, Find all the tchotchkes and antiques you want at the neighborhood’s annual yard sale in Latrobe Park. June 2, 8 a.m.-12 p.m.

Federal Hill Jazz & Blues Festival, in nearby Federal Hill, will feature more than 12 bands on two stages, as well as arts and crafts, food vendors, and kid games. June 3, 11 a.m.-7 p.m.

Star-Spangled Sailabration, the weeklong celebration to mark the War of 1812’s bicentennial, features many events in Locust Point, including an air show, public ship tours, and concerts and fireworks at Fort McHenry. June 13-19.


Population: 2,458 Median home price: $106,000 Own-to-rent ratio: 48.6 to 51.4 percent Miles from downtown Baltimore: 2.6

Those whose only pass through Remington on their way to or from I-83 are missing out. Bounded on the west by Sisson Street, the south by 21st Street, the east by N. Howard Street, and the north by Wyman Park, the ‘hood is a bastion of blue-collar Baltimore. In recent years though, Remington has been embraced by younger generations, eager to repurpose its vacant industrial spaces for their own artistic and altruistic functions. Perhaps the most notable example of this is Charm City Cakes, the bakery made famous on the Food Network’s Ace of Cakes reality show, filmed at its 6,000-square-foot compound at the corner of Remington Avenue and W. 30th Street. Across the street is one of Baltimore most-beloved bars, The Dizz, which sells Charm City Cakes merchandise for the tourists but lures locals with its excellent bar food and unpretentious atmosphere. The New Wyman Park Restaurant—–which is not new and actually a diner—–is similarly down to earth, while the neighborhood’s other diner, the Papermoon, ups the quirk-factor with its eclectic décor and menu. Locavores love the new Baltimore Food Co-op, which carries local produce and national brands like Annie’s Naturals and Kashi. For gluten-free goodies hit up bakery Sweet 27, and complement your guilt-free dessert with organic coffee or tea from Charmington’s, where the baristas can top your cup with milk-foam designs. Charmington’s is also notable for its location on the ground floor of Miller’s Court, an old tin-can factory renovated into state-of-the-art office, retail, and living spaces. Apartments are available to Baltimore-area schoolteachers at discounted rents, and office space is leased to nonprofits such as Teach for America and Playworks. But Remington hasn’t gone soft. Just across the street from Miller’s Court is the Ottobar, the city’s stalwart rock club that’s never met a mohawked musician it didn’t welcome. We just wonder what the punks think about the soon-to-be-built 25th Street Station shopping center, which will be anchored by, yes, a Wal-Mart.


As of June, the Baltimore Streetcar Museum is open both Saturday and Sunday from 12-5 p.m. Regular admission is $7 and includes unlimited rides on original Baltimore streetcars.

Wyman Park Dell will be ground zero for this year’s Charles Village Festival featuring live music, a 5K race, and a block party. June 2-3. The Ottobar hosts Insubordination Fest 2012, three days of prime underground punk, pop-punk, and power pop. June 21-23.


Population: 5,544, Median home price: $559,000*, Own-to-rent ratio: 76.5 to 23.5 percent, Miles from downtown Baltimore: 17.6 (*Sparks median home price courtesy of Krauss Real Property Brokerage)

Sparks is a perfect slice of Maryland countryside in central Baltimore County. Though the community’s borders are somewhat amorphous, it is generally accepted that it encompasses land within a two-mile radius of I-83 north of Hunt Valley and south of Route 138/Monkton Road. It is an area of considerable natural beauty with rolling pastures sloping down to the winding Gunpowder River along which the 20-mile Torrey C. Brown Trail (aka the NCR trail) meanders, offering hiking, biking, horseback riding, and fishing. Before casting your line, stop by Great Feathers for your rods and reels and to ask the fly fishermen on staff what’s biting. Drive along Belfast, Sparks, and Lower and Upper Glencoe Roads for good views of the many working and gentlemen’s farms that dot the landscape. Make sure to swing through the Oldfields School campus, a picturesque all-girls private high school with a stellar equestrian program. Sparks also boasts the U.S. headquarters of sportswear giant FILA as well as offices of McCormick & Company. This combination of rusticity and sophistication is reflected in the neighborhood’s two main restaurants. First, there’s The Filling Station, an old gas station turned coffee shop serving delicious soups, salads, and sandwiches during the day. Then, there’s The Milton Inn, which offers fine dining housed in a circa 1740 fieldstone Colonial that was once an all-boys school whose pupils included John Wilkes Booth. During the summer, locals relax at Basignani Winery, a family-run vineyard that hosts frequent events.


The MAC Half Marathon & Two-Person Relay takes over the NCR trail on May 19.

Basignani Winery has outdoor movie nights (including wine tasting and popcorn!) May 25, June 8 and 22, July 6 and 13, and August 3, 24, and 31.

Kids ages 6-12 will explore the Gunpowder River at Stream Search/Aquatic Exploration on June 23, 9-11 a.m.

West Annapolis

Population: 734 Median home price: $737,200 Own-to-rent ratio: 74.6 to 21.3 percent Miles from downtown Baltimore: 25.4*
*West Annapolis statistics courtesy of

The New Annapolis

If you can’t afford to take that big trip this spring or summer, think about sticking closer to home with the ultimate “staycation” in Annapolis, only a half-hour drive away. Now more than ever, our state capital has exciting things going on. Here are just a few:

Test Your Luck
The first phase of Maryland Live! Casino at Arundel Mills—–which will feature 4,750 slot and electric table games, like blackjack, roulette, craps, and poker—–is scheduled for completion in June.

Wine and Dine
Wine bars are all the rage in the Annapolis area this year. Red Red Wine Bar on Main Street is a tough table to get with its funky, bohemian design. And Vin 909 in Eastport takes an organic, seasonal approach with its ever-changing menu.

Getting Around
Naptown went pretty green last summer with the introduction of two car-free ways to get around. Electric-bike shop Green Pedals moved to West Annapolis last summer. Also, the town’s new City Circulator trolley trots people from the various shops and restau-rants, all for $1 a ride.

Set Up Shop
The gargantuan Annapolis Towne Centre seems like it keeps expanding, but that doesn’t stop boutique shops and eclectic stores from making their mark—–everything from Poppy and Stella and Urban Chic to Paper Source and Charm City Run.

The peninsula northwest of downtown Annapolis has started to have an identity all its own. Separating itself from the preppy, naval stereotypes of the state capital, West Annapolis is a tiny, bohemian community. The hippie vibe is evident in the establishment of wellness centers like Ridgely Retreat, which offers advanced spa treatments, yoga and dance classes, and acupuncture. There is also West Annapolis Art Works, which has framing services and an eclectic gallery of pieces, like waterview paintings, political cartoons, and African sculptures. And, if you’re so inspired, there is supply store Art Things, stationery shop Pris’ Paper, and Tara’s Gifts for kitschy presents and party décor. For a quick bite, there’s the eco-friendly b.b. bistro, which uses only local and seasonal ingredients. For potent margaritas and huge portions, try Mexican Café. There’s also Regina’s Restaurant which features unlikely, but welcome, German cuisine. There are plenty of places to go antiquing in this small community, like Bon Vivant Antiques, which specializes in online sales, and West Annapolis Antiques, which features jewelry and furniture from estate sales. Spending a day browsing the shops along Annapolis Street makes you feel like you’re in a quaint New England town, instead of the heart of Maryland. But, of course, the Annapolis influence isn’t too far away as the Navy-Marine Corps Memorial Stadium is down the street and is jam-packed with football fans every fall. There are plenty of activities (and prime real estate) along the water, so many residents can be seen crabbing, kayaking, or sailing on the Severn River. The close-knit community seems like the best of many worlds—–a classic yet progressive small town with no shortage of things to do.


Cinco de Mayo is the town’s first celebration of this Mexican holiday. Look for margaritas and sangria, Latino music, and vendors selling their wares. May 5, 10 a.m.-5 p.m.

Paris Flea Market is a unique event where the town turns into a Parisian-style market, and they close off Annapolis Street and have residents buy a space and sell whatever old artifacts they want to get rid of. June 23, 8 a.m.-4 p.m.

Oktoberfest is the biggest West Annapolis event and will be celebrating its 22nd year. They close the street and have 140 vendors and feature German bands, beer, and food from Regina’s Restaurant. September 23, 10 a.m.-5 p.m.