2020 Gift Guide

By Susan Moynihan

Holiday celebrations may be quieter this year due to social distancing, but that doesn’t make the season any less special. For this year’s gift guide, we’re spotlighting six towns that are ideal for shopping day trips, with picks from independent stores sure to please the names on your Nice List. 

If you prefer to stay home, they all offer delivery, as do the other local picks on our online holiday shopping guide.

Its roots are in the Revolutionary era (evidenced by the stately Georgian homes in and around the waterfront), but quaint Chestertown is modern as well, with a deep love of the arts. A bevy of independent shops and galleries makes it a great place to find one-of-a-kind gifts for the creative set on your list. 

For Shopping

Make your first stop Twigs and Teacups, a destination gift shop. You can’t help but smile as you wander their whimsical assortment of clever home goods, tchotchkes, coffee-table books, and more. Massoni Gallery is a must for fine-art lovers. Owner/curator Carla Massoni’s longstanding relationships with artists gives her better access to works than you find at big-city galleries in New York. The aptly-named Create sells high-end, American-made pieces from a curated collective of artisans specializing in exquisite glassware, sculpture, woodwork, and jewelry. MusicLife Delmarva has instruments from ukuleles to brass, plus sheet music and lessons for all levels.

For Sustenance

The weekly Farmers Market, held Saturdays from 8 am to noon, features area produce and handcrafted items from soaps to pottery. Any time is a good time to pop into Evergrain Bread Company, where every crusty loaf, sweet scone, and fresh focaccia is baked onsite. (The coffee’s great, too.) Chester River Wine & Cheese offers a tasty selection of cheeses, charcuterie, specialty pastas, marinades, local meats and more. Or leave the cooking to the pros with a meal at The Kitchen at the Imperial, a perennial winner of CBM’s Best of the Bay awards. 

For Something Extra

Their popular A Dickens of a Christmas weekend has been postponed until 2021, but you can still enjoy strolling the town and checking out the festive decor on historic homes and storefronts— and you may run into some pop-up musical performances as well. 

The county seat for Talbot County is the geographic and economic center of the lower Eastern Shore, and the gateway to smaller towns like St. Michaels, Oxford, and Tilghman Island, serving millionaire estates, rural towns and generations-old farms alike. Which means there’s a little something for everyone in this commercial crossroads, tucked into tidy storefronts in the historic downtown. 

For Shopping

Crackerjacks has toys for kids of all ages, from clay crafting kits and Ravensburg puzzles to plush friends in every size and species, including breed-specific pooches. Silver Linings specializes in Chesapeake-themed jewelry, with the expected crabs and anchors but also sterling boat cleats, canoe paddles, workboats, and watermen’s boots represented. Invest in heirloom-quality crystal and porcelain at Benjamin, or fine-art sculpture or landscape at award-winning Troika Gallery. Albright’s Gun Shop has all you need for hunting season, from SITKA waders to Barbour jackets for man, woman and dog. Check off your favorite bibliophile’s wish list from the beautifully curated titles at Flying Cloud Books.

For Sustenance

Easton’s thriving food scene has loads to tempt you, be it fresh salads at Sunflowers & Greens, wine by the glass and small plates at The Wardroom, or classic Eastern Shore cuisine at Hunter’s Tavern. Piazza Italian Market offers direct-from-Italy groceries and wine for gifting, plus tasty paninis, soups, and pastas to enjoy there or take home. Rise Up Coffee Roasters was founded in nearby St. Michaels, and their Organic Maryland roast (or take-home, five-flavor starter kit) will keep you going all season long.

For Something Extra

Moonlight Madness takes over downtown on Friday, December 4, with carriage rides, a crafts market, a town raffle, and loads of holiday cheer.

This charming town sits at the very top of the Bay, and its walkable downtown of late 19th and early 20th century buildings is a great place to find unique gifts for history lovers. On your stroll, don’t miss the colorful murals on Market Street, which showcase the city’s past as a stop on the Underground Railroad and as a horse-racing center. (George Washington and Seabiscuit both slept here.)

For Shopping

Washington Street Books & Music has two stores’ worth of collectibles, from used books and vinyl to games and toys. Don’t miss their collection of authentic movie costumes, displayed behind plexiglass in rotating exhibits. Mary L. Martin Ltd. vintage postcards span the 1940s through the 1970s, and are a great way to personalize a gift, or recall a treasured memory. Pyrex fanatics come from all over to peruse the collection at JoRetro, which spans over 1,000 pieces in every size and hue. You’ll also find contemporary, retro-minded gifts like tea towels and linens, Havre de Grace pillows, candles (and Mandles—candles for men), and mid-century modern clothing and furniture. The husband-and-wife team at Vincenti Decoys Painting and & Supply have been creating beautifully detailed decoys of waterfowl, songbirds, and shore birds for 40 years. Their shop has their work, as well as the work of other regional artists. Bearwood Designs features cool metalwork, furniture and jewelry by another talented artist duo, Mike and Renee Lust.

For Sustenance

Vineyard Wine Bar specializes in smaller, family-owned vineyards with a great taste of place. Sample the ever-changing varietals by the glass and half glass, or peruse their bottle shop for takeaway. For the best views in town, grab a bite on the lawn overlooking the Susquehanna at Tidewater Grille and dig into a plate of chicken Chesapeake or surf ’n’ turf. Bomboy’s Candy has been making and selling candy for more than 40 years. Create a mix-and-match box and try not to eat them all on the way home.  

For Something Extra

Havre de Grace’s Holly Jolly First Friday and tree lighting takes place on Friday, December 4. For 2020, the annual candelight tour of homes is now a candlelight tour of porches, held Saturday, December 12, from 4 to 8 pm. 

One of the oldest towns on Virginia’s Eastern Shore, Onancock is a great excuse for a road trip any time of year. Capt. John Smith called it the Gem of the Eastern Shore back in the early 1600s, and to this day, what it lacks in size it makes up for in charm. Get your bearings and more history at the circa-1842 Hopkins Brothers Store, a former mercantile center now run by the Eastern Shore Historical Society.

For Shopping

Get set for holiday entertaining at North Street Market, where cheery Blue Crab Bay Company dishes, smartly packed serving sets, and a great selection of imported cheeses, infused oils, and vinegars make great hostess gifts. Photography fans will love the striking aerial landscapes from At Altitude, or pick up a delicate seascape by Laura MacGowan or a colorful folk scene from Danny Doughty, two notable local artists. You can customize a sterling silver Chesapeake Bay bracelet with onsite engraving at family-owned C.D. Marsh Jewelers.

For Something Extra

For 2020, the town is debuting Believe: A Christmas Driving Tour, with two miles of lights, music, and live characters, running Saturday, December 12 from 4 to 8 pm.

For Sustenance

Get a warm welcome at the Blarney Stone Pub, along with a pint, fish and chips, and live music. Or head out on the deck at Mallards at the Wharf for water views, great seafood, and possibly a song by chef-owner Johnny Mo, who’s known to serenade diners with his guitar when he gets a break from the kitchen. Don’t leave town without stopping into Corner Bakery for freshly baked donuts, and a package of sweet potato biscuits to go. 

This friendly town in the center of Virginia’s Northern Neck is the perfect place to slow down during a hectic holiday season. The pedestrian-friendly downtown is made for ambling, and Town Centre Park lights up with decor and music every weekend evening starting December 10.

For Shopping

Kilmarnock Antique Gallery is home to the Oyster Plate Lady, and what’s said to be the country’s largest collection of these beautiful, highly collectible dishes. Pick up a one-of-a-kind terrarium filled with succulents and spiky air plants—or better yet, build your own—at Grow NNK, which also sells custom CBD oils and lotions. The Rivah has a devoted fan base, thanks to their great staff and ever-changing selection of covetable goods like Bogg Bag and Simply Southern totes, Lily Pulitzer dresses and masks, and colorful costume jewelry. Find fun gifts including printed tumblers, journals, and bar towels along with a stellar selection of cards and stationery
at Papeterie

For Sustenance

Grab an outdoor table for a pint of locally made cider and charcuterie at Ditchley Cider Works, set in an historic, 160-acre estate. Old-school eatery Lee’s has been serving up hearty diner-style plates and homemade pies for 80 years. NN Burger has been voted Best Burger in VA for seven years running, and their shakes have to be seen to be believed. Specials Wine Cellar has the largest selection of bottles in the region, to enjoy by the glass or to go.

For Something Extra

The Kilmarnock Trolley Express, a 90-minute “enchanted journey” to the North Pole (based on the book The Polar Express), runs the evenings of December 4 and 5; timed tickets required in advance.

The town of Historic Yorktown is anchored on one side by the American Revolution Museum at Yorktown and the York Battlefield on the other. In between is Riverwalk, a modern, pedestrian-only town square overlooking the York River. Step back in time and learn a bit about how holidays were celebrated in our nation’s earliest days.

For Shopping

The shop at the American Revolution Museum at Yorktown has gifts galore, from reproduction period glassware and painted chargers to felt ornaments of George, Thomas and Alexander. Folk artist Marilyn West (aka Auntie M) upcycles vintage fabrics, wool, metals, and more into everything from wall hangings to cuddly toys, which she sells along with crafts from other regional artists at Auntie M’s American Cottage. Artist Henry “Hank” Viccellio Goldsmith creates unique, intricate designs, including his signature Yorktown bracelets, at Viccellio Goldsmith & Fine Jewelry. Have an idea for a design? He does custom work, too. 

For Sustenance

Warm up with freshly baked cookies and a cup of Deadrise coffee at Mobjack Coffee, set in the circa-1730 Cole Digges House. Enjoy fresh seafood, burgers, and salads at Yorktown Pub, just across from the York River public beach. Since you’re so close, pop over the bridge to Gloucester, home to the original Whitley’s Peanut Factory, for VA-grown nuts, brittles, and barks. 

For Something Extra

The Christmas Market on Main, held on December 5-6, features 60-odd vendors, strolling entertainers, roasted chestnuts, and the Big Man himself. The smaller Mistletoe Market comes to town on December 12.