Events and Things to Do Around Town

The town of Rock Hall, Maryland is affectionately known as the ‘Pearl of the Chesapeake’. We’re not sure how that came to be, but we can tell you that it is certainly a gem. Rock Hall continues to embody and honor its waterman’s and farming traditions, almost like a throwback to a different era. Somehow, even the light here seems special, as the many artists in the area will attest. You can experience these traditions by partaking of charter fishing trips and sailing excursions on Chesapeake Bay, bike touring, walks in our nature preserves, visiting historic points of interest, sipping wine at one of our Eastern Shore vineyards, nosing around galleries and shops and of course, cracking steamed crabs and/or eating at any one of many restaurant choices (every one of which makes a great crab cake!).

Rock Hall Annual Events – (check blog page seasonally for details)

May – Spring BikeFest, Triathlon
June – National Music Festival, Rockfish Tournament
July – July 3rd Fireworks, July 4th Parade, Waterman’s Day
August – Pirates and Wenches Weekend
October – Waterman’s Triathlon, Fallfest
November – Country Craft Guild Show
December – Winterfest, New Year’s Eve Rock Hall Crawl & Hat Parade & Rockfish Drop

Rock Hall Treasures Hunt!

Come see all the surprising treasures our town has to offer by playing our scavenger hunt challenge during your stay with The Inn at Huntingfield Creek. It’s our take on discovering the not-so -obvious things around the Inn and Rock Hall in a new, fun and creative way. Winners receive a $50 certificate towards their next visit and bragging rights on our Facebook page!

*Header image provided courtesy of Jen Davis.

Music and Arts

Mainstay, Rock Hall
The Mainstay is a warm friendly place with great sound and sight lines. With only 120 seats, there’s not a bad one in the house. With over 50 annual concerts, Mainstay features a variety of musical offerings, something for everyone. Beer, wine and soft drinks are available. Our audiences range from local Rock Hallers to those who find their way here from Philadelphia, Annapolis, Baltimore, Washington DC and beyond. 5753 N Main St, Rock Hall, 410-639-9133.

The Garfield Center for the Arts at the Prince Theatre
A wonderful theater presenting a wide range of concerts and live performances of jazz, live theater, dance, as well as films. 210 High St, Chestertown, 410-810-2060.

Church Hill Theatre
A performing arts center dedicated to the creation and presentation of quality performance and educational opportunities. History, events and productions. 103 Walnut St, Church Hill, 410-758-1331.

Chester 5 Movie Theatre
Chester 5 Movie Theater in Chestertown. 21 Washington Ave, Chestertown, 410-778-2227.

First Friday
Meander the red-brick, tree-lined sidewalks of Historic Chestertown, while enjoying extended shop hours and arts and entertainment throughout Downtown. For a list of activities, please check this calendar for specific listings.

An active organization promoting the arts in Kent County featuring a multi-artist gallery and gift shop in Downtown Chestertown. 315 High St, Chestertown, 410-778-6300.


Kent Museum
Kent Museum was organized in the 1960’s to preserve Kent County’s rural heritage. Local farming families have donated agricultural equipment and household items from the past. Over 200 items depict the life and livelihood of rural living. On display are antique tractors, horse drawn wagons and sleds, and household gadgets that helped the farm wife with her chores. 13689 Turner’s Creek Road, Kennedyville, MD 21645. 410-348-5543.

Waterman’s Museum
This museum is dedicated to the Watermen of the Chesapeake Bay whose heritage plays a great role in the history of Maryland’s Eastern Shore. Hours: open 7 days a week 10 am-4 pm and by appointment; key available at the Ditty Bag Store in the main building at Haven Harbour Marina, 20880 Rock Hall Ave, Rock Hall, 410-778-6697.

Chesapeake Bay Maritime Museum
The Chesapeake Bay Maritime Museum is a non-profit organization dedicated to telling the stories of the Chesapeake Bay and the people who have shaped their lives around it. Situated on 18 waterfront acres in the historic town of St. Michaels, Maryland, the Museum offers exhibits, demonstrations, boat rides on the Miles River, and annual festivals that celebrate Chesapeake Bay culture, boats, seafood, and history. 213 N. Talbot St., St. Michaels, MD 21663, 410-745-2916.

Restaurants and Eateries

Java Rock
Gourmet coffeehouse with delicious breakfasts and ‘something different’ lunches, wine boutique and eclectic gifts. Perfect for people watching with a pet-friendly deck. 21309 E Sharp St, Rock Hall, 410-639-9909.

Inn at Osprey Point
Fantastic waterfront restaurant in Rock Hall. Wednesday-Sunday, dinner starting at 5pm, 20786 Rock Hall Avenue, Rock Hall 410-639-2194.

Durding’s Store
An original old-fashioned soda fountain (circa 1925) serving delectable soda fountain treats and homemade baked goods. 5742 N Main St, Rock Hall, 410-778-7957

Waterman’s Crab House and Dock Bar
Enjoy sea food in a waterfront dock bar environment in view of the Chesapeake Bay. Open 7 days a week from lunch through dinner during the summer season. Live music on the weekends. 21055 Sharp St, Rock Hall, 410-639-2261.

Harbor Shack
Waterfront Bar and Grill located in Rock Hall Harbor. Menu includes choice cuts of Angus beef, a wide variety of local seafood entrees and Mexican dishes. Live entertainment on weekends. 20895 Bayside Ave, Rock Hall, 410-639-9996.

Bay Wolf Restaurant
Bay Wolf Restaurant is a mix of Austrian and Eastern Shore Cuisine. A local favorite! 21270 Rock Hall Ave, Rock Hall, 410-639-2000.

The Imperial Hotel Restaurant and Bar
The Imperial Hotel Restaurant and Bar in Chestertown serves brunch, lunch and dinner. The food is described as “eclectic contemporary cuisine” drawing on a variety of culinary disciplines and focused on fresh regional ingredients. 208 High St, Chestertown, 410-778-5000.

Fish Whistle
Waterfront Dinning for lunch and dinner in Chestertown. Full service bar. 98 Cannon St, Chestertown, 410-778-3566.

Evergrain Bread Company
Evergrain Bread Company in Chestertown specializes in European-style artisan bread and pastries. Also serving soups, sandwiches and coffee. Open Wednesday-Sunday from 7:00AM–5:00PM. 201 High St, Chestertown, 410-778-3333.

Cafe Sado
Nicely appointed authentic Thai restaurant also featuring an impressive selection of fresh sushi. 870 High St., Chestertown, 410-778-6688.


Check out the Indulgences of the Eastern Shore!

The Inn Pool
Enjoy a relaxing day by the I@H/C saltwater pool.

Flow SalonSpa
Flow Salonspa is an Aveda Concept Salon. Aveda’s plant-derived products providing a perfect balance of eastern wisdom and western science to nurture your body, soothe your senses, and quiet your mind. 305 High Street, Chestertown, 410-810-1881.

Excellent full service hair, make-up and nail salon at 400 so. Cross St. in Chestertown, 410 810-0009.

Crow Farm and Vineyard
Taste award winning wines of the Eastern Shore in the Crow Vineyard tasting room. 12441 Vansants Corner Rd., Kennedyville, 410-648-5687.

Shopping in Rock Hall
Shopping in Rock Hall is an exciting adventure that encompasses the entire downtown and waterfront. There are antiques, jewelry, clothing, fishing gear, marine supplies, kayaks, Rock Hall souvenirs and memorabilia. Recommended are The Hickory Stick and Java Rock, both near Sharp and Main. Stop by The Village stores at Rock Hall Ave. and Main St. for eclectic gifts and treats. Bayside Grocery store is a small but comprehensive full service market at the same intersection.

Farmers Market in Chestertown
On Saturday mornings from 8 am to noon, located in beautiful Fountain Park in the heart of downtown Chestertown, on Maryland’s Eastern shore you’ll find wonderful fresh home grown produce, herbs, breads, soaps, plants and cut flowers as well as the hand-crafted works of local artisans.

Kent Athletic & Wellness Center
An all purpose fitness facility for all ages and all fitness levels. Indoor sports, racquetball, zumba, ballet, yoga, personal training, rooms for strength, weight training and cardio fitness. 800 High Street, Chestertown, 410.778.3148.

Sweet Cheeks, Delightful Treats
Decadent handcrafted chocolates, cookies and other irresistible offerings. Yellow cottage in Village Shops, Rock Hall 410 639-7037

Outdoor Activities


Blue Crab Charters provides a memorable 1-1/2 hour sail on the Bay including complimenatry beverages. An excellent value and customer favorite! At the foot of Sharp St. by Watermans Restaurant.

Fishing and Boat Rentals

Still known as one of the premium blue crabbing locales in the state, East Neck Boat Rental will rent you the boat, nets, and bait as well as any other supplies you might need to have a great day on the water.

Fish the Chesapeake Bay with one of the East Coast’s most professional, top notch charter fishing outfits with Fish Fear Us.

Chesapeake Dolphin Charters offers a select fleet of prime charter boats for your next cruising get-a-way. Their fleet is located in Rock Hall, which has the distinct advantage of being a prime cruising location on the Eastern Shore. Top-rated gunkholing and anchorage favorites are within a short cruise of Rock Hall.


Kent County is bounded on the North by the Sassafras River, on the South by the Chester River, and the Chesapeake Bay to the West. All that adds up to great places to explore by kayak or canoe, with Chester River Kayak Adventures in downtown Rock Hall, be sure to give it a try. Or, borrow one of Inn at Huntingfield Creek’s complimentary kayaks and start paddling!


Learn to sail on the beautiful Chesapeake Bay. Instruction available at: Maryland School of Sailing, Rock Hall Yacht Club, Rock Hall, 410-639-7030.


Kent County, with its gently rolling landscape and lightly traveled roads, is ideal for cycling. Please ask us for biking maps of the area. See Birding and Biking. Also, Inn at Huntingfield Creek offers 2 nice bikes/helmets for complimentary use.

Horseback Riding

Lovely trail rides are available at the Kent Equestrian Center 410-778-1881. Private instruction and rides are available at Humphreys Point Farm just outside Rock Hall, 410 708-9184.


Waterfowl hunting is synonymous with Kent County, the Winter home of the largest Canada geese migrating population on the Eastern Flyway. Canada geese, snow geese, ducks, doves, pheasants, quails can all be hunted through various outfitters. Ask InnOwner Jim for contact information.

Nature Trails and Hiking Opportunities

All the below are simply a short drive away, should you want to explore the wildlife habitat of the Eastern Shore (and you should!).

Eastern Neck Wildlife Refuge
Just five minutes from the Inn at Huntingfield Creek, this 2,285-acre island refuge is a major feeding and resting place for migrating and wintering waterfowl. Wintering home to the Arctic Tundra Swan, more than 100,000 ducks, geese and other waterfowl seek sanctuary here each year, as do migrating and breeding songbirds and shorebirds. American Bald Eagles nest and thrive here year-round. 1730 Eastern Neck Rd., Rock Hall, 410-639-7056.

Sassafras River and Turners Creek Natural Resource Management Area
1,000 acres of farmland, mature forests, sandy beach, tidal ponds and marshland. Nature trails, open fields, and a waterfront bluff overlooking the Sassafras River. See waterfowl, songbirds, eagles, deer, beaver, muskrat, raccoon, woodchuck. 13761 Turners Creek Road, Kennedyville, 410-820-1668​.

Millington Wildlife Management Area, Maryland-Line Road, Massey
4 ponds stocked with bass and bluegill within 3,800 acre preserve. Hiking, bird and wildlife watching, mountain biking. See woodpeckers, woodcocks, scarlet tanagers, and beaver. 410-928-3650.

Wye Natural Resources Area
2,800-acre preserve on an island featuring nature trails and a wide variety of wildlife viewing. 632 Wye Island Road, Queenstown, MD 21658, 410-827-7577.

Chesapeake Farms Wildlife Habitat
Chesapeake Farms Wildlife Habitat is a 3,300-acre preserve with a wonderful self-guided driving tour and is home to a variety of birds, deer, fox, bald eagle etc. 7319 Remington Drive, Chestertown, 410-778-8400.

Adkins Arboretum
Adkins Arboretum is a 400-acre native garden and preserve on Maryland’s Eastern Shore dedicated to promoting the appreciation and conservation of the region’s native plants. Five miles of paths along streams, through meadows and native plant gardens, and under the shade of a rich bottomland forest attract nature lovers, gardeners, students and birders. 12610 Eveland Road, Ridgely, MD 21660, 410-634-2847.

Blackwater National Wildlife Refuge
Blackwater National Wildlife Refuge is located on the Eastern Shore approximately 12 miles south of the town of Cambridge. The Refuge includes over 27,000 acres, composed mainly of rich tidal marsh characterized by fluctuating water levels and varying salinity. Other habitat types include freshwater ponds, mixed evergreen and deciduous forests, and small amounts of cropland and managed impoundments that are seasonally flooded for waterfowl use. 2145 Key Wallace Drive, Cambridge, MD 21613, 410-228-2677.

Bombay Hook Wildlife Refuge
Located adjacent to Delaware Bay and covering 16,251 acres, Bombay Hook Wildlife Refuge provides habitat for wildlife. The refuge is a tidal salt marsh with a mix of meadows, mud flats, tidal pools, rivers, creeks, and tidal streams. The upland area includes forests, freshwater impoundments, brushy and timbered swamps, and fields of herbaceous plants. This diversity of habitats is reflected in the diversity of animal life. The refuge offers visitors a 12-mile wildlife drive, five walking trails (2 handicapped accessible), three observation towers, wildlife photography, hunting opportunities, a variety of nature and educational programs, and interpretative displays. 2591 Whitehall Neck Road, Smyrna, DE 19977, 302-653-9345.