Weekend adventure: A visitor's guide to Rock Hall and its old-school, waterfront charms

Turn down Main Street in Rock Hall and go back to a time when everyone in town knew your name.

The historic Eastern Shore watermen's town — population 1,298 — is a charming throwback to a forgotten age of neighborly affection and good-natured fun, rather than technological distractions. Tiny bed-and-breakfasts, an old-fashioned soda shop and plenty of vintage and antique spots dot a quiet and quaint Main Street.


"This is really a weekend town," said Annette May, who owns The Tangerine Shop antique store and has lived in Rock Hall for decades. The town is busiest on weekends, she said, when tourists and locals alike stroll Main Street and pop in and out the variety of shops offering clothing, sweet treats, furniture, gifts and more.

But more than a shopping district, Rock Hall is a "very, very fine boating community," May said.


Known as the "Pearl of the Chesapeake," this Kent County locale is a bayside town through and though. Miles of coastline, a public beach and more than a dozen marinas offer a variety of nautical adventures. Waterside restaurants serve fresh seafood dishes on outdoor docks with a view of the town's famous sunset.

"If you came to watch TV, sorry, I don't know what to tell you," said Sandy Scott, a business owner and Rock Hall resident. "But there aren't better sunsets anywhere else."

During a day there recently, Rock Hall proved a picturesque and peaceful place with the potential for old-fashioned fun. For those who want to make the trip, here's a primer of what to do and see, where to dine and stay and more.


Swan Creek Gallery & Studio

Christine and Dan O'Neill opened a gallery and wood shop in their home when they moved to Rock Hall and have been displaying their personal artwork in the gallery ever since. After spending the better part of seven years sailing in the Bahamas, the Maryland Institute College of Art graduates established their Rock Hall home to display their sea- and nature-inspired paintings, photographs and woodworks. "We both just love the water and water-insprired things," Christine O'Neill said. As is customary in Rock Hall, the gallery keeps weekend hours when the artists are available. Inquire for prices. 21026 Rock Hall Ave. 443-822-9153,

The Mainstay Performing Arts Center

With its well-loved couches and gaggle of mismatched chairs, The Mainstay makes music from around the world feel intimate. Catch a $10 concert on Mainstay Mondays or plan ahead and grab a ticket to one of their forthcoming shows. Open Saturday and Sunday most weeks. Check their online calendar for event times. 5753 Main St. 410-639-9133,

Eastern Neck Wildlife Refuge


A quick drive takes Rock Hall visitors to the Eastern Neck Wildlife Refuge, a 2,285-acre island with seven hiking trails, three areas for fishing and plenty of wildlife, including the bald eagle, to spot. For avid bikers, the heart of the refuge is an 8-mile ride from Main Street in Rock Hall. Winter visitors can catch a glimpse of the refuge's migrating tundra swans. Open year-round, 7:30 a.m. until 30 minutes after sunset. 1730 Eastern Neck Road. 410-639-7056,

Fishing Charters

Asked why a water-lover should choose Rock Hall specifically, Gratitude Marina service manager Wade Hague said, simply, "Well, because it's Rock Hall!" Most of the slips in the "quiet little fishing town" are full early in the year, Hague said, but there are plenty of opportunities for those without their own boats to catch their dinner, or at least try. More than a dozen charter boats take fishing novices and experts alike out on the Chesapeake Bay for a chance to snag a local rockfish. Rates vary by company.

Family Activities

Rock Hall Yacht Club Family Sail

Learn how to sail with the whole family. Rock Hall's Yacht Club offers a two-hour sail with a trained instructor that will tailor the lesson to your family's needs. No experience necessary. Up to four people can register for a lesson, but there must be at least one adult and one child. $169 per party. Call for an appointment. 22759 McKinleyville Road. 410-775-8225,

Blue Crab Chesapeake Charters


Take a sunset ride on the Chesapeake. Aboard the Crab Royale, Capt. Mark Epstein runs 90-minute tours every two hours, starting at 10 a.m. and ending at 4 p.m. The sunset cruise begins one hour before sunset. Cruises run between April 1 and Oct. 30. $35 per person. Cruises leave from Waterman's Crab House at 21055 W. Sharp St. 410-708-1803,

Bayside Landing Park and Pool

After a day of shopping and sailing, watch the boats out on the Chesapeake or cool off with a swim. The Bayside Landing Park and Pool is open to the public and just yards from sparkling Rock Hall Harbor. Pool open Thursday through Sunday, noon to 7 p.m. Free to the public. Call 410-778-7439 for information about boat ramp.

Rock Hall Public Beach

Known to locals as Ferry Park, the beach is small but offers a place to rest by the water and watch the sun melt into the bay. The rock jetty-flanked spot features a few charming white gazebos, picnic benches and a view of Baltimore's skyline across the water. There are no lifeguards, so swimming is at the visitor's discretion. Beach is open all hours. Parking available off Beach Avenue.


Hickory Stick


Wine racks, Vera Bradley purses, Simply Southern clothing and a personal favorite, Chef Marla's spices ($8.95 each), can be found at this eclectic boutique. Co-owner Sandy Scott opened the Rock Hall location in 2009 and has loved the store, and the town, ever since. She was nervous about bringing in boatwood pieces — furniture made from out-of-use boats. "We're not a furniture store," she said, but visitors often marvel at the colorful works (a reclaimed mirror goes for $242 and an armchair fashioned from a hull goes for $972). "They don't go every day, but they're something unique," Scott said. Monday through Friday 10 a.m. to 5 p.m.; hours vary seasonally. 21326 Sharp St. 410-639-7980

Village Quilting

A quilt shop in 2017? Yes, and an impressive one at that. Quilters from all over the world stop into Village Quilting, said Kat Fithian, a Rock Hall resident who works in the colorful store. Rock Hall is a big quilting town itself, Fithian said, and boaters stop in to gather supplies for long trips out on the water. Open 10 a.m. to 4 p.m. Monday through Friday, 10 a.m. to 7 p.m. Thursday, 10 a.m to 3 p.m. Saturday, 11 a.m. to 3 p.m. Sunday. 5701 N. Main St. 410-639-4101, search "Village Quilting" on Facebook.

The Tangerine Shop

Annette May's antique shop is a microcosm of what the town has to offer. Jewelry made from from sea glass, books by local authors, nautical paintings and woodcarvings by Eastern Shore carvers populate the one-room store in Rock Hall's shopping village. "People bring in things," May said. "If I like them, I buy them." Open Thursday-Sunday, hours vary. 102 Rock Hall Village. 410-639-7009

Vintage Picnic


Everything necessary to build a perfect beach picnic is waiting at this shop. Pick from baskets, dishware and all the necessary accessories or bring family heirlooms to design a custom picnic set. Open 4 p.m.-7 p.m. Fridays, 11 a.m.-5 p.m. Saturdays, 11 a.m.- 4 p.m. Sundays. 105 Rock Hall Village. 703-568-1062,

Eats and Drinks

Sweet Cheeks

Immaculate-looking sugary treats sparkle from behind a glass counter in this micro-sized sweet shop. Sweet Cheeks offers cakes, cookies, truffles and artisanal donuts — including a new, sugar-free blueberry oatmeal flavor. Open Monday and Thursday-Sunday, hours vary by day. 103 Rock Hall Village. 410-639-7037,

Harbor Shack

Here's where you should go to eat like a local. Harbor Shack is a place where the bartenders know every customer's drink order, said co-owner Donna Walls, and everyone is like family. This town favorite is a harborside spot with an extensive menu of Mexican and seafood eats (the shrimp and asparagus quesadilla is a delicious mix of the two) and live music every weekend. Put away your cellphones, the menu warns — this is a place for good company, good food and no worldly distractions. Open 11:30 a.m. to 9 p.m. Monday, Wednesday-Thursday, 11:30 a.m.-10 p.m. Friday-Saturday, 10 a.m.-8 p.m. Sunday. Bar open later. 20895 Bayside Ave. 410-639-9996

Waterman's Crab House


For 21 years, Waterman's has served up a variety of fresh fish, boat-to-table crabs and dinner with a dockside view. Open 11 a.m.-8 p.m. Sunday–Thursday, 11 a.m.-10 p.m. Friday-Saturday. Bar open later. 21055 W. Sharp St. 410-639-2261,


A throwback to simpler times, this circa-1925 shop with a traditional soda fountain serves up milkshakes, ice cream, light lunch fare and bulk penny-candy. Open 10 a.m.-6 p.m. Sunday-Thursday, 10 a.m.-8 p.m. Friday, 10 a.m.-9 p.m. Saturday. 5742 N. Main St. 410-778-7957.

Java Rock

Whether you have a refreshing iced coffee, a soothing macchiato, a fresh-pressed panini or a glass of wine in mind, this eccentric cafe is the place to find it. Enjoy your food and drink and shop for gifts inside the store, or sit out on the patio and chat with the locals. Open 7 a.m.-4 p.m. Monday-Thursday, 7 a.m.-5 p.m. Friday-Saturday, 7 a.m.-3 p.m. Sunday (summer hours). 21309 E. Sharp St. 410-639-9909,




This five-suite hotel is a clean and quaint old-timey spot. Each suite is equipped with a bathroom and kitchenette, and guests can lounge on the second-floor deck or hunt for antiques at Gallery Gifts downstairs. Rooms range from $135 to $155 a night. 5750 N. Main St.

Inn at Osprey Point

This inn on the water features seven elegant suites with a double or king bed and a private bath in each. The inn has a fine-dining restaurant and 160-slip space dock for transient boaters. Rooms range from $130 to $250. 20786 Rock Hall Ave. 410-639-2194,

Inn at Huntingfield Creek

Nestled amid fields of sunflowers and lavender, behind a secluded river and beside a woodside pond, this high-class inn pulls out all the stops. Rooms come with memory-foam topped mattresses, WiFi, down comforters, antique hardwood floors and welcome treats. Seven private cottages are also available. Rooms range from $175 to $230. 4928 Eastern Neck Road. 410-639-7779,



Pirate and Wenches Weekend

For one weekend every summer, tiny Rock Hall explodes with life as thousands of tourists from across the state flock to the Pirates and Wenches Fantasy Weekend. For those dressed in their best seafaring garb, there are rum-drinking contests, a buccaneer's ball, and the dinghy race — a local favorite, said Walls. She opens the Harbor Shack early during the event, and her whole staff dresses up. "Everyone from the littlest pirate to the oldest is dressed up," including dogs, she said. Pirate and Wenches Fantasy Weekend is Aug. 11 through Aug. 13.

By the Bay Car Show

Hot rods and classic cars parade through Rock Hall while competing for trophies and Best of Show. Take in the sight of these chrome coaches while enjoying music, food vendors and raffles. Sept. 2, runs 9 a.m. until crowds disperse. Free to the public; $10 to register a car. 410-639-2428.

Waterman's International Triathalon

One of two triathalons hosted on Rock Hall each year, the Waterman's International Triathalon takes athletes on a 6.2-mile run, a 25-mile bike and 1,500-meter harbor swim. Spectators can enjoy a bouncehouse and music from a professional DJ. Athletes can also join a sprint competition, relay or a half-triathalon. Sept. 30 and Oct. 1, race times vary. $125 registration fee for full triathalon.


Fall Fest

In its 20th year, this celebration of Rock Hall offers visitors music, craft vendors and oysters — plenty of oysters. 10 a.m. to 4 p.m. Oct. 14. Free.