Leslie Stevenson, the doyenne of The Avenue, with her shiny shampoo-commercial hair, dimpled smile, and signature spectacles, opened her beloved shop, In Watermelon Sugar, at a friend’s nudge.

Stevenson’s pal was launching an Italian deli at the corner of Chestnut and 36th Street in Hampden but only wanted half the space. “Why don’t you open up a little home furnishings store,” she suggested.

And that’s really all it took.

“I signed a lease without knowing anything,” she says, laughing.

At the time, Stevenson, who grew up in Ruxton and graduated from the Maryland Institute College of Art, had worked at the Wine Merchant slinging sandwiches and at Dvorine Associates, a high-end design firm on Falls Road. “I’m sure my father was just absolutely ready to keel over and die because he knew I had no experience whatsoever.”

Nevertheless, she persisted and signed a lease. “I did everything backwards,” she says. “I did no research. I had no knowledge of business—I went to art school. I just knew what I liked. And what looked good together.”

Even when it came to the name for her new business, Stevenson was unruffled. “Not having had this lifelong dream to open a store, I had no thoughts on a name, so I was like, ‘Does anybody have a good name for me?’”

The crowdsourcing worked and a friend, who was a huge Richard Brautigan fan, suggested In Watermelon Sugar, Brautigan’s post-apocalyptic novel set in the aftermath of a fallen civilization. She thought it sounded colorful and wonderfully vague, since she still wasn’t quite sure what her store was going to sell. Her naivete most likely saved her from panicking.

“There were plenty of times where I feel like I probably should have seen the writing on the wall,” she says, referring to signs that the business might not be a success. “But I didn’t because I did not have that knowledge to know when to say when. So, I just kept plugging away.”

She emphasizes that she could never have done 25 years on her own. Stevenson gives all the credit to her support system—her husband, Bill Stevenson, the owner of Waverly Tattoo; their 16-year-old son, Xan, who grew up at the shop; and the people of Hampden, who have shopped in her store and welcomed her to the community. Everyone but herself.

“She’s so self-effacing, so chill,” says Libby Francis-Baxter, who owns the Modest Florist across the street and serves as the Hampden Village Merchants Association’s vice president. “She never takes credit for anything.”

But anyone who has stepped foot inside the magical corner shop, with its sunlight dancing across the wood floors, knows it’s all Stevenson. It’s clear in the store’s East-Coast-meets-West-Coast vibe, its perfectly placed displays, and even in that unmistakable scent—is she piping it through the air vents?—that smells like pure happiness (and a kiss of coconut). Her merchandise sits firmly between whimsical and practical. There are candles and cards, trinkets and baskets. Each nook holds books and room sprays, jewelry and lamps. There’s always a stack of seafoam-green or chocolate-brown tissue paper for wrapping gifts and her telltale pink sticker on each bag and box. And no matter how times you’ve walked through the shop—even just the day before—there is always something new to find.

“I think I was her first customer,” says Cameron Barry, who was working at the Mill Centre in 1998 and would pass by the shop every morning and afternoon. “I’m sure I just drove by and decided to check it out— and the rest is history.” She’s been a loyal shopper ever since. “I’ve never seen Leslie sit,” says Barry. But Stevenson never hovers either, allowing customers to peruse at their own pace. “She’s just incredibly warm and welcoming,” says Barry, “and has an interesting selection.”

Barry has story after story of Stevenson pointing her in the direction of other Hampden businesses instead of trying to force a sale. “Go next door,” she told Barry when she was looking for a mirror. When Barry told the folks at the Antique Exchange Stevenson had sent her, they said, “We love Leslie—she’s always sending people over here.”

Francis-Baxter isn’t surprised. She considers In Watermelon Sugar an “anchor institution” for Hampden—part of that first wave of businesses that turned the neighborhood into a shopping mecca and continues to be one of its biggest draws.

“She’s got an incredible eye—there’s no question. Anyone who has ever walked by her windows, you just stand there in awe,” says Francis-Baxter. But, she says, the windows are just an entry point into Stevenson’s world. “She’s really got the insight into those things that make you feel good and make you want to give good.”

The storefront windows on Chestnut weren’t always part of the equation. Remember those friends who encouraged her to open a shop next to their deli? In an ironic twist, they closed their business a year after Stevenson opened hers, and the landlord gave her the chance to take over the entire space. (“All the murals of the Sistine Chapel that are on the walls were left over from the Italian deli,” says Stevenson, clearing up something inquiring minds have often wondered.)

Initially Stevenson was hesitant, but her father insisted. He told her if she ever wanted to grow her business, which she would have to do in order to survive, she’d need room for more merchandise and storage. “I mean, none of this stuff entered my brain,” admits Stevenson. “So thankfully, it entered my father’s. He got me started on the right path—in every way.” They put a doorway between the two spaces, and it was a pivotal moment for the shop. She started selling less hand-painted flea market finds and more eclectic home goods. And she started to get a feel for who her customers were.

“Hampden is a unique area in the sense that you get so many different people,” she says. There are the college kids, folks from nearby Guilford and Homeland, tourists who find their way to The Avenue, plus a huge swath of regular customers that constantly come back, because they rely on Stevenson for certain staples. “Sometimes it’s hard, because you’re trying to accommodate all these people. But it’s also what’s great, because you have so many different types of people coming in.”

“IT’S HARD TO THINK OF ANYTHING ELSE OTHER THAN BEING GRATEFUL.”

Stevenson was 28 when she opened the store and now sits squarely in her 50s. “There’s a big difference between your mindsets. I don’t think you’re capable of absorbing the magnitude of time at that age. I don’t even think I had an idea when I opened the shop—how long am I going to be here? It just seemed like the next best move. Like, you live in the moment at that age, and everything is new and fun.” At that point, In Watermelon Sugar was her whole life. She’d work, close up, go out to bars, and rinse and repeat. There were no obligations other than making sure she was there the next day to turn the key.

Now she understands the weight of owning a business, having employees, paying bills, placing orders, and a new wrinkle: surviving during a pandemic. “There were times when I wished I had a boss, you know, someone to tell me what to do,” she says with a wry laugh. The freedom that came with owning a business—“I’m in control”—was also the burden that kept her up at night.

Other (fun) stresses include those beautiful seasonal windows where Stevenson really lets her creative juices flow. She realized early on she couldn’t put too much inventory inside the windows because the sun would bleach the goods, so instead she started creating displays with the product being almost secondary.

“It’s fun, but after 25 years it’s a little stressful only because I feel like I’ve done so many themes.” She starts rattling off previous fall windows—“I’ve done mushrooms, owls, woodland, farmers market, apple-picking, pumpkin patch… ” The shop’s basement is full of random items she’s collected for over two decades. Friends bring her rocks, branches, moss, and stumps for potential use in the window. And she’s caught the bug, too. She laughs. “I mean I can’t walk around outside without being like, ‘Ooh.’”

Indeed, on her frequent trips to California to visit her sister, she’ll often ship back boxes of rocks. Everyone is on the hunt. “Even my brother-in-law would be out surfing and find these crazy rocks and shells. And he’d box him up and send them to me for display. I know it’s ridiculous, but you open a business, and it just becomes all-consuming.”

But somehow Stevenson still makes it look effortless—like she’s almost embarrassed this milestone anniversary would cause any sort of fanfare. And in true Stevenson fashion, it’s her shoppers she’s focused on.

“It makes you reflect on your own life, when you see an anniversary for somebody that’s sort of big, because all of a sudden, you’re like, I’ve been going there for 25 years.” She’s watched customers have babies and now those babies are graduating high school or driving themselves over to shop for a girlfriend. “It’s a weird position that you don’t think of when you open something in your 20s. So, in your 50s, you reflect back. It’s hard to think of anything else other than being enormously grateful that you’re still there, and you’re able to witness this passage of time and see these people that you wouldn’t normally see unless you had a shop. It’s definitely wild.”

She also knows how lucky she is—especially during those darkest days of COVID-19. “I mean we lost Trohv,” she says solemnly. “And because we lost Trohv, I feel like I’m sort of reaping the benefits.” So that was sort of a bittersweet fluke. “[There are] a lot of variables that go into measuring success. And I think it’s not always [about] patting yourself on the back, thinking that you did the right thing.”

But when pressed, Stevenson says she does allow herself the occasional moment to soak it all in.

“I’m lucky to be in a neighborhood where I know so many people and they’ve kind of become a family. There’s a sense of ease that comes after 25 years. So, it’d be a shame to leave that now.”

For the foreseeable future, her plan is simply to keep showing up and turning the key.

“I’m grateful to have this to come to every day,” she says.

It’s safe to say that 2020 wasn’t a banner year for fashion. Fashion week was a bust, and the best most of us could muster was cozy chic. But this year, we’re planning to make a splash back into the social scene. Our inspiration? Anything bright and airy from our favorite Baltimore boutiques. Here are a few pieces to add to your mood board:

➜ Clothes

THE PIED PIPER. Thanks to high- end brands like Ella Moss, Lilly Pulitzer, and Polo, tiny fashionistas ock to this one-stop shop in the Village at Cross Keys. The store offers a wide variety of styles, with sizes for children ages infant through 14. Village Square, 410-435-2676

WEE CHIC. If you are looking for the latest designs and gear for your toddler or tween, consider taking
a drive to Green Spring Station to check out the goods at Wee Chic. With clothing, candy, bags, books, and toys, there’s something for every age and size kid in this store. 2360 West Joppa Road, Lutherville-Timonium, 410-878-7400

BELLE BAMBINI. Serving the Baltimore community for more than 10 years, Belle Bambini Children’s Boutique has everything from suits and occasion wear to pajamas and onesies for your mini-me. The store carries sizes from infant to teen
and is even developing a section for moms. The experienced and friendly staff will make sure you never leave empty-handed. 1330 Reisterstown Road, 410-653-5437

THE LILY PAD OF TOWSON. If you don’t want to spend a fortune on clothes your children will quickly grow out of—or if you have a closet full of stuff that doesn’t t any of your kids—the Lily Pad of Towson is the place for you. Whether you’re looking to consign or to shop, this store specializes in gently used and affordable kid’s clothing and furniture. 6907 York Road, Towson, 410-377-0025

AWW BABY ORGANICS BOUTIQUE. With a mission to sell only the best eco-friendly products, Aww Baby Organics Boutique does all the work for you when it comes to finding quality items that are environmentally safe for your growing family. 8600 Foundry Street, Savage, 443-540-8377

TINY TOES. Tiny Toes is a one-of-a-kind children’s store situated among the quaint boutiques on Bel Air’s Main Street, offering clothes, swimwear, and accessories. Considered a Harford Country treasure, the shop focuses its efforts on providing the community with only the highest-quality merch for kids. 4 North Main Street, Bel Air, 410-420-6727

BABY PEA. Baby Pea Clothing specializes in pint-sized outfits for all occasions, from family photos to baby showers, weddings, and more. But the best part? If you don’t see an ideal design for your baby pea, they will create a fresh one for you! Based out of Damascus, Baby Pea Clothing is not exclusive to babies, with designs for teens and even adults.

➜ Toys

SMART KIDS TOYS. Great for teachers and conscientious parents, Smart Kids Toys is dedicated to the learning development of children. In addition to timeless favorites, the store has educational activity books and placemats, as well as remote-control cars and outdoor activity sets. Run by the former owner of Learning How, it’s the place for unique and high-quality toys. 11121 York Road, Cockeysville, 443-286-4975

AMUSE TOYS. With a carefully curated selection of cool stuff to play with, aMuse Toys is a go-to store for kids. But these toys are more than just fun distractions. Offering award-winning, smart toys from around the world, aMuse encourages creativity and innovative thinking for children aged newborn to 10-plus. 1623 Thames Street, 410-342-5000

➜ Bookstores

THE CHILDREN’S BOOKSTORE. Recognized as one of the top 50 indie bookstores in America by The Huffington Post, this Lauraville bookstore carries children’s chapter books and illustrated books of various genres for a range of ages. A hub for young readers, The Children’s Bookstore also partners with local schools for book fairs and author book signings. 4717 Harford Road, 410-532-2000

OLD FOX BOOKS. Seeking that rare quiet afternoon with the kids? Old Fox Books & Coffeehouse is where you’ll want
to go. Little ones are able to browse books while you grab an afternoon caffeine pick-me-up. When the weather is nice, settle out on the back patio for a magical garden view and relax with a good read. 35 Maryland Avenue, Annapolis, 410-626-2020

B. Willow to open in Canton
After two years of laying down roots on West 27th Streetin Remington, everyone’s favorite plant palace, B. Willow, is opening a second location in Canton. The two-story space just off O’Donnell Square will host their already excellent array plants and terrariums, as well as a selection of furniture and home goods from Cedar & Cotton, a local company specializing in new and vintage furnishings. We have a feeling that everything in this store will spark joy. Sorry Marie Kondo. 2822 O’Donnell St.

Radcliffe Jewelers thrives in new Kenilworth home.
This past September popular local jeweler Radcliffe made the move from Towson Town Center to The Shops at Kenilworth and has been received with open arms—and more parking spaces. After over 30 years in the mall, Radcliffe is happy to be in a new space that has a real community feel with other local retailers like Ruth Shaw, About Faces, and South Moon Under. Along with their new digs, this location offers styles from Rolex, David Yurman, and many more. Keep an eye out for upcoming trunk shows and their big annual sale in April. 800 Kenilworth Dr., Towson, 410-321-6590

Poppy and Stella to open in Old Ellicott City
Fells Point favorite Poppy and Stella announced they will be opening a location in Old Ellicott City this April. The store, which was once home to toy store All Time Toys, will feature a similar assortment of shoes, apparel, accessories, and gift items from brands like Sam Edelman, Knot Sisters, and Dolce Vita to name a few. Follow along on social media for more details on the new store and an opening date. 8185 Main St., Ellicott City

Cohen’s Clothier closes after 115 years in business
It’s the end of an era for preppy style institution Cohen’s Clothier. After 115 years in business, the shop announced via Facebook earlier this month that it would be closing its doors for good. Originally located on South Broadway in Fells Point, Cohen’s was first opened in 1904 by Max Cohen and has stayed in the family as it evolved, expanded, and relocated to its Cockeysville location. In a message to his customers, owner Gilbert Cohen explained that their current lease was up and that the time had come for him to retire. “Goodbyes are never easy,” states Cohen. “But the satisfaction of filling a need in our community for so many years will remain.” 64 Cranbrook Rd. 410-666-8020

While December often hits Baltimore with slick sidewalks and the occasional heap of sooty snow, winter settles gently over Maryland’s Eastern Shore. Quiet harbors slowly ice in, waves of Canadian geese float in endless Vs over the stubble of empty cornfields. Here, the holidays are spent with family and friends, your wool socks kicked up by the woodstove, and your spoon scraping the dregs from a mug of oyster stew. It’s a place where the year’s bitter end is celebrated by traditions glowing with the patina of time and a connection to community, to the landscape, and to the Chesapeake Bay.

There’s never a better time of year to trade the glare of crowded shopping malls for something more authentic on the other side of the Bay Bridge. Whether it’s a crisp, rosy-cheeked foray to pick the perfect Blue Spruce, the electric glow of a crab basket Christmas tree, or a muskrat diving into the New Year, there’s something sure to spark every seasonal spirit, humbugs and all.

Winter Waterland

In Baltimore, we have our hub caps, but across the Bay, nothing says “Happy holidays!” with a stronger Eastern Shore accent than a Christmas tree made of crab bushel baskets—an iconic piece of Chesapeake culture.

On December 1 at 5 p.m., kick off the seasonal festivities with a sky-high (and frankly spectacular) example that lights up at the beginning of the annual Cambridge Christmas Parade. A Dorchester County tradition for 70 years, it is a truly timeless piece of Chesapeake Americana and small-town nostalgia at its best. Held in the heart of the historic district, it features marching bands playing covers of “Jingle Bell Rock,” local kids throwing candy from sparkling floats, and Santa riding on a fire truck.

On December 1, Rock Hall gets in on the action with the lighting of their very own crab basket tree after Santa’s arrival via fishing charter boat. Welcomed by eager crowds and accompanied by live music courtesy of the local community marching band (including one hand-shaking, baby-hugging mascot crab), Saint Nick makes his way Pied-Piper-style from the public landing to Main Street, where he’ll post up near the tree to take requests from those on his Nice List.

On December 8, Tilghman Island gets in on the action at the Phillips Wharf Environmental Center with the lighting of another unique Eastern Shore Christmas tree—this one made of hundreds of stacked wire crab pots—followed by one of the shore’s several illuminated boat parades. Watch from the shoreline as the island’s floating fleet of classic Chesapeake workboats, including deadrises, skipjacks, and other iconic vessels, shed their work-day dredges for a splashy array of holiday lights that reflect softly on the bay.

Yuletide Tunes

If you think Christmas carols simply mean sweetly corny songs, funny bonnets, and that one tone-deaf singer never quite hitting his or her notes, you’ve never experienced the magic of classic holiday jams given the Postmodern Jukebox treatment.

On December 1, check out Motown & More, A Holiday Celebration at Easton’s venerable Avalon Theatre, where a six-piece ensemble of musicians and vocalists with serious chops redefine the meaning of Christmas slay with smooth covers of old favorites such as “Santa Baby” and “Silent Night.” The vintage hits keep coming on December 7 when the Avalon also hosts the Glenn Miller Orchestra Holiday Show. This iconic 18-member troupe is a time-machine to the era of Bing Crosby crooners and Big Band swing-dance classics, with plenty of throwback holiday favorites mixed in.

For a concert that covers more than just Christmas, check out Chester River Chorale’s December 1 concert up the road in Chestertown for arrangements of Chanukah and Christmas songs in a celebration of both the secular and the sacred.

Party Like Charles

If you do enjoy classic Christmas carols, be sure to visit Chestertown from December 7-9, when the Kent County town embraces its inner Fezziwig during the second annual Dickens of a Christmas Festival.

From top hats to plum pudding, fire dancers to Dickens-inspired street theater, Chestertown goes full Victorian all weekend long. Partake in a “Run Like the Dickens” 5K, participate in family-friendly gingerbread house workshops, tour historic houses, take afternoon teas, and attend a costumed 19th-century ball sure to be packed with bustles and waistcoats. On Saturday evening, High Street transforms into an open-air jubilee featuring live entertainment, microbrews, and convivial, communal fire pits—a perfect way to start the evening before heading to a performance of (what else?) Tiny Tim’s A Christmas Carol at the Garfield Center for the Arts.

Farther south, Berlin also celebrates the holidays with an entire month of Victorian Christmas with a decorated downtown, old-fashioned carriage rides, live music, and late-night shopping.

Shop ’Til You Drop

The Eastern Shore has plenty of festive alternatives to perfunctory online shopping—no coupon codes necessary. Pick up something special IRL (that’s “in real life,” to the non-millennials) at these hometown holiday shopping events infused with local spirit.

On December 2, head to Kennedyville in Kent County for the Rivers to Canal Wineries Holiday Sip & Shop. Hosted by Crow Vineyards from Kent County, as well as Broken Spoke Vineyards and Chateau Bu-De from Cecil County, the vino-fueled fete is a great place to both taste new local wines and pick up a few bottles of your favorites for top-notch stocking stuffers.

If your vibe is more Etsy than Amazon, make way to Talbot County on December 7-9 to check out St. Michaels’ Marketplace and Sweet Shoppe, hosted by the town’s year-round Christmas store, for an old-school holiday bazaar. Browse original paintings, handmade jewelry and toys, one-of-a-kind decorations, and homemade jams and pies, all made by local artisans. Some of the proceeds go to a good cause, so don’t be afraid commit to the Season of Giving by grabbing a few extra collectors’ ornaments.

For more shopping, some favorite local gift stores include Twigs & Teacups in Chestertown, Piazza Italian Market in Easton, Bay Country Antiques in Cambridge, and Gilbert’s Provisions in Berlin.

Deck The Halls

Let’s be honest: nobody wants a sad, dried-out Charlie Brown Christmas tree or a plastic wreath. Channel your inner Clark Griswold on a search for the freshest you-cut-it tree or sweetly scented garlands at some of the shore’s best farms and outdoor festivities.

Throughout December, Blue Heron Tree Farm in Centreville provides all the necessary equipment—from saws to wagons—for wandering through grassy rows of conifers on this 12-acre property in Queen Anne’s County. Pick up fresh greens or a tree stand while warming up with a hot cocoa in the onsite barn before heading back to Baltimore.

For folks tracking farther south, Cawley Family Farm in Denton has plenty of gorgeous spruces, pines, and firs to choose from, including lots of freshly harvested, pre-cut specimens in their barn. This Caroline County farm also offers custom wreaths made to order onsite, so call in advance to pick your perfect trimmings—just don’t forget the oyster shells!

Looking for a more natural approach to holiday greenery? Check out the Holiday Wreath Sale & Open House at Adkins Arboretum on December 1, where handmade decorations crafted from the Arboretum’s forests and gardens are available only once a year. Don’t miss the event’s pop-up art and pottery shop by local artists Irene and Paul Aspell, followed by a walk through the Arboretum’s winter landscapes to the Wildlife Tree, an evergreen decked with birdseed pinecones to sustain local feathered friends through the long winter.

Island of Misfit Toys

Sometimes you need a break from all the holiday pomp and circumstance. There’s only so many fruitcakes you can reasonably eat, after all. Break away from the ordinary with a few refreshingly unconventional approaches to the Most Wonderful Time of the Year.

On the evening of December 7, visit Layton’s Chance Vineyard and Winery in Vienna for Ugly Christmas Sweater Karaoke. Undoubtedly, the worse the sweater and the singing, the better the evening, so order a couple glasses of wine and commit to some seriously terrible renditions of “Baby It’s Cold Outside,” all in good (bad) fun.

Meanwhile, on December 14, you can mount up in Salisbury for the Bike Party: Holiday Lights Tour. This monthly cycle social will take a unique two-hour route to check out the Wicomico County town’s best light displays. Riders are encouraged to make their own spectacle by festooning themselves and their wheels in lights, garlands, bows, wrapping paper, ugly sweaters, menorahs, dreidels, and Seinfeld Festivus Poles, undoubtedly leaving a sea of amused onlookers in their wake.

Diving Into 2019

The lower Eastern Shore has long been defined by its abundant marshes, and in celebration, the lowly swamp-loving muskrat has been elevated to darling status in Dorchester and Somerset counties. No surprise, then, that the muskrat makes an appearance during the holiday season—and this time, not on a dinner plate.

On the last night of the month, head down to Princess Anne for perhaps the most tongue-in-cheek New Year’s Eve send-off on the entire Eastern Shore: The Midnight Muskrat Dive, kicking off at 9 p.m. In this wonderfully weird free event, a muskrat dressed for the occasion in a top hat and cape is hoisted to the top of a zip line for the stroke of midnight while the townspeople celebrate the end of 2018 with music, oysters, and Smith Island cake. Then, with great fanfare, “Marshall Muskrat” flies like a rat out of hell over their heads and down the street. Suddenly, it’s 2019—in the most eccentric, Eastern Shore way ever.

See also: Rock Hall’s Rockfish Drop, Easton’s Crab Drop, Cambridge’s Boat Drop, as well as a classic Ball Drop in both Berlin and Salisbury.

→ BREAKFAST

Whatever the hour, start your day at Chick & Ruth’s Delly, a stalwart breakfast counter for homemade pies, award-winning crab cakes, and massive platters named after local politicians. (Order the “Congressman Elijah E. Cummings” for a one-pound ham steak, two eggs, potatoes, and toast.)

→ MORNING

The best way to get to know “Naptown,” as its locally known, is to go off and explore. Partake in various Watermark walking tours to learn about African-American heritage or ghost lore, or hop aboard a classic Woodwind schooner to admire the city by water. We also recommend meandering the likes of Main Street and Maryland Avenue for historic-home browsing and boutique shopping (especially at McBride Gallery, KA-CHUNK!! Records, and Annebeth’s wine shop).

→ LUNCH

For your midday meal, it’s all about local seafood. At City Dock, grab a street-side booth at the circa-1740 Middleton Tavern—once patronized by founding fathers George Washington, Thomas Jefferson, and Benjamin Franklin—for people watching, oyster shooters, and lump-filled crab dip. For more world-class crab cakes, try Davis’ Pub in Eastport, while Cantler’s Riverside Inn across the Severn River is your destination for hard shells.

→ AFTERNOON

Often called a museum without walls, Annapolis is a history buff’s version of bliss. On State Circle, the Maryland State House once housed the Continental Congress and still serves as the General Assembly’s gathering place today. For more colonial history, saunter through the verdant gardens of the William Paca House and Historic London Town in nearby Edgewater. Of course, no trip is complete without a visit to the U.S. Naval Academy. Before football season rolls around, tour the grounds, museum, and campus chapel, where you can view the crypt of John Paul Jones, aka the father of the U.S. Navy.

→ DINNER

To experience the best of the city’s restaurant renaissance, start with happy hour at Sailor Oyster Bar for craft cocktails and fancy takes on fish before moving onto your main course at Preserve. This farm-to-table eatery, featured on our list of 50 Best Restaurants, focuses on sustainable sourcing and seasonal dishes such as grilled Maryland blue catfish or coffee-glazed local beef. Enjoy dessert a few doors up at the Annapolis Ice Cream Company, with homemade flavors including blueberry and Key lime pie.

→ EVENING

Live music abounds in Annapolis, with the original Rams Head Tavern featuring premier acts such as Taj Mahal and the Kingston Trio on its intimate stage. (On July 31, catch Baltimore’s own Thomas Dolby of “She Blinded Me With Science” fame.) Also check out the Metropolitan Kitchen & Lounge for up-and-coming artists, and the Annapolis Maritime Museum for summer evening concerts. The Annapolis Summer Garden Theater is another nightlife must, with al frecso plays beneath the stars.

A People United

Sells tribal-influenced products that are handcrafted by women in underdeveloped countries, like Nepal. The store gives back by donating profits to help support schools for children in Nepal.
516 N. Charles St., #100, 410-727-4471

Antique Row Stalls

A 10,000-square-foot antique and art gallery, with items including furniture, lighting, and decorative art like paintings and sculptures.
809 N. Howard St., 410-728-6363

For Rent Shoes

Offers urban street-wear-inspired pieces, including a large variety of sneakers, hats, casual clothing items, and other accessories for men and women.
515 Cathedral St., 443-873-9928

Gian Marco Menswear

Specializes in men’s European designs from dressy sport coats and classic button-downs to cuff links and bow ties.
517 N. Charles St., #1, 410-347-7974

Linden Heights Ave

Combining retail and art, the store sells an eclectic mix of gently used clothing as well as VHS movies and vinyl records.
810 N. Calvert St., 404-428-1942

No Pins Framing and Presentation

A professional framing store that also offers artistic restoration and supplies.
10 W. Eager St., Ste. 101, 443-224-3171

Noveau Home and Interior Design

The home-goods store and interior-design firm moved back to its roots in Mt. Vernon in January. It also revamped its image, now fusing modern glamour with reclaimed vintage style.
10 W. Eager St., 410-962-8248

Paris West Optical

High-end optical boutique that provides complete eye exams and stylish eyewear.
521 N. Charles St., 410-528-1877

reUP Home

Designs furniture and artwork, using recycled and upcycled products, converting trash into treasures.
519 N. Charles St., 443-682-1179

Strongbox

Offers a unique collection of modern and vintage pieces, including abstract art, home décor, and accessories like bow ties and hats.
802 St Paul St., 717-525-3682

The Doll House Boutique

Serves as a place for shoppers to score on clothes made by local designers. The store also offers stylists and custom dresses.
525 N. Charles St., 443-874-7900

The Zone

Vintage and consignment shop offers an array of clothing and accessories, such as neon wigs and fur coats. This is the go-to store for vintage styles from the ’60s to the ’90s.
813 N. Charles St., 410-539-2817

City Cafe
The perfect place to re-caffeinate or grab lunch between shopping destinations.
1001 Cathedral St., 410-539-4252

Dooby’s
A Baltimore favorite for that midday coffee, grub, or pastry craving.
802 N. Charles St., 410-609-3162

Milk & Honey Market
Offers local farm-to-table items in its full service cafe with a separate organic grocery section.
816 Cathedral St., 410-685-6455

The Bun Shop

A cozy cafe with the best culturally-influenced buns in town.
239 W. Read St., 410-989-2033