July 14, 2022

Road Trip to the Small Harbor Towns on Maryland’s Eastern Shore 

Katie and Gene Hamilton

Bring Binocular News

Play, stay and stargaze in Chestertown, Rock Hall, St. Michaels, Tilghman Island, Oxford and Cambridge 

The harbor towns on the Eastern shore of Maryland are known for crab feasts, maritime history, boating, biking and craft beer. You’ll find plenty of wineries and distilleries, too. But the historic towns on the water are also hidden gems for stargazing with low lights, boundless vistas and in-town lodging. They offer places to play, stay and stargaze in quaint harbor towns of the Chesapaeake Bay.

While these towns are popular day trips from Baltimore, Washington D.C. and Philadelphia we’re suggesting you’ll find plenty to do day and night. While some of these towns are known for their lively bar scenes we found some have a split personality and offer an alternative quieter side especially nice for solo and family visitors. 

Going north of the Bay Bridge to Chestertown, Rock Hall and Chestertown

From the Kent Island side of the Chesapeake Bay Bridge it’s a 35-mile drive through rural farmlands to Chestertown on the shores of the Chester River in Kent County. This historic town, home of Washington College, has several inns and B&Bs in and around town with a tasty mix of restaurants and specialty shops.

A visitors center provides plenty of local knowledge and information about daytime activities like a self-guided walking tour of historic homes, chartering a boat or browsing the work of local artists in town.

 Chestertown is the home of the Sultana Education Foundation which has grown from building a replica of the 1768 schooner Sultana in the late 1990s to an extensive education center with programs in history, wetland preservation and citizen science studying natural resources. Visitors often take canoe and kayak tours on the Chester River.     

At the foot of High Street the town landing has a boardwalk lining the shore so it’s an easy walk from an in-town stay. The river walk is lighted with sensitive down facing lights that provide safety without spreading light into the open sky. Sit on a bench, aim binoculars up to the sky and enjoy the stars. From Wilmer Park on the river watch the night sky from the community parkland off of Cross Street.

Visit Main Street Chestertown for information.

Rock Hall

The charming laid back town Rock Hall is some 13 miles down Hwy 20 with an atmosphere different from the historic neighborhoods in Chestertown. Rock Hall is a working waterman’s town being gentrified, and you can’t miss the local small town feeling. As a popular boating center off the Bay, Rock Hall boasts two harbors, one in town and the Haven just outside of town. The town is small with an eclectic collection of stores that attracts visitors and weekenders. From town it’s a short walk to the harbor with marinas, inns and motels and waterfront dining venues. See a fishing shanty with all the paraphernalia used by early watermen from the early days of crabbing, fishing and oystering at the  Waterman’s Museum in town. Come night time you’ll find good stargazing spots anywhere along the harbor and at Ferry Park.    

Rockhall Avenue (Hwy 20) leads to Osprey Point at the Haven north of town with more boating facilities and upscale lodging and dining. The road wraps around to Beach Road with cottage rentals overlooking a small beach and an expansive view of the Chesapeake, another stellar place for stargazing.    

Visit Rock Hall for information.

Going south of the Bay Bridge to the Bay Hundred Peninsula

If you cross the Bay Bridge and turn south on route 50 (toward Ocean City) you’ll find more stargazing opportunities in Talbot County at St. Michaels, Tilghman Island and Oxford.  St. Michaels and Tilghman are part of what’s called the Bay Hundred area. “Bay Hundred” comes from Colonial days when Maryland was divided into districts that supported 100 militiamen. Today you’ll see it as the moniker of several businesses in the area. Being surrounded by water the Bay Hundred peninsula boasts wide stretches of farm fields and a healthy seafood industry.

St. Michaels

St Michaels is a gentrified waterman’s town known for its crab restaurants, maritime museum, specialty shops and eclectic eateries, many on the water. Sample local rum and whiskey distilleries and craft beer and wine. Rent a bike or enjoy a walk on the covered bridge trail or explore the slow pace of neighborhood streets.

The Chesapeake Bay Maritime Museum showcases the rich history of marine heritage with the Hooper Island Lighthouse on its grounds. By day you can rent paddle boards, ski boards, kayaks, anything that floats. Or take a cruise of the Miles River on the Patriot tour boat or sail on Selene II, a 42-foot restored 1926 gaff-rigged sailing yacht. Another option is the harbor water taxi and escape boat tours.

You’ll find more good places in town for night sky viewing at Muscrat Park overlooking the harbor with picnic tables and benches. (Thursdays in summer go to the concert in the park.) Take a short walk through the neighborhood of historic homes toward the school to the end Seymour Street where a small park overlooks the Miles River, ideal for night viewing.

A visitors kiosh in town has plenty of local information or go to St Michaels to plan a visit.

Tilghman Island

Tilghman Island, an easy 15 mile drive from St. Michaels, is a small community of watermen, local islanders and retirees who favor fishing and boating. A drawbridge over Knapps Narrows separates the mainland from the island and provides a nice setting for waterfront inns and restaurants. Fishing charter boats leave from Knapps Narrows so does the popular tour of Poplar Island to see the reclamation of a near submerged island being brought back to life and purpose with dredging from Baltimore Harbor. It’s a fascinating tour showcasing an environmental initiative operated by the US Army Corps of Engineers, Maryland Dept. of Transportation and Maryland Environment Service. For information call 410/770-6503 or email poplartoursmenv.com.

The Wylder resort (formerly Harrisons) just beyond the Narrows overlooks the open sky and Choptank River. Sit on a lawn chair and you’re ready for the night sky. Visit Tilghman Island for more information.

Our firsthand experience using binoculars when traveling: 8×25 compact binoculars are a good choice for traveling because they’re lightweight and easy to tuck into a backpack or purse. The first number”8” is its magnification which makes an image 8 times closer than what you see with your eyes; it’s good for a wider field of view. The “25” is the size of the objective lens measured in millimeters that defines how much light the binocs can gather. A larger objective lens has more light gathering power so the image resolution will be higher and brighter.                      


You can drive to Oxford from the Easton Bypass off route 50 or take the Oxford-Bellevue Ferry, a car ferry from Bellevue near St.Michaels. The ferry takes passengers on a short trip across the Tred Avon River to Oxford, another small waterfront harbor town. If St. Michaels is a wild child, Oxford is her quiet sister because this charming village is as popular with boaters as it is with bicycle riders. A few shops and fine dining keep visitors coming back to small inns and B&Bs and the historic Robert Morris Inn.

The Water’s Edge Museum on Mill Street, within the Oxford Think Tank, welcomes visitors with a rare collection of paintings and lithographs depicting the stories of the lives and work of Black families on the eastern shore. The museum embraces history, culture, art and environmental justice and celebrates the rich diversity in Maryland.

Oxford is a walkable village with narrow streets so it’s an easy walk from an in-town stay to the water’s edge at the Oxford Wharf at the ferry dock. Watch the sky from there or walk farther down The Strand to the small beach and peruse the night sky facing the town harbor. On Morris Street across from the Treasure Chest gift shop the town park faces the Tred Avon River where you can sit on a bench and enjoy the view. For more information go to Port of Oxford.



Driving to Cambridge on route 50 pass over the Choptank River and you’re greeted by a magnificent mural of Harriet Tubman on a building. Harriet Tubman lived in the area and the Harriet Tubman and the Underground Railroad National Historic Park puts Cambridge on the map of the significant contributions of Black Americans. The museum itself is expansive and comprehensive and well worth a visit.  The driving tour of the Underground Railroad Byway takes you on country roads from Cambridge to Goldsboro on a network of trails, waterways and safe houses used by escaping slaves as they fled to northern states.  

Cambridge is known as the city of murals because beautiful paintings are splashed across buildings throughout downtown streets peppered with specialty retailers, micro-breweries, wineries and B&Bs. Foodies find a nice selection of local eateries and seafood spots and fine dining restaurants. On the river in town you’ll see the long history of its maritime heritage at the Richardson Maritime complex and Ruark Boatworks and its history of the fishing industry at J.M. Clayton Seafood Company.

The marina park and Long Wharf Park on the harbor are nearby with the skipjack Nathan of Dorchester ready to take on passengers. Fishing charter boats moor there, too.

Just outside of town is the Hyatt Regency Resort located upriver from the harbor.  The resort offers all the amenities you’d expect in a luxury hotel with many rooms with balconies overlooking the river. Enjoy the open grounds and stroll along the riverfront walkway or sit in Adirondack chairs on the lawn and appreciate the quiet surroundings. Just a few miles away is Blackwater National Wildlife Refuge, another popular stop for nature lovers.

To learn more about Cambridge and the area go to Dorchester County

Maryland’s eastern shore proximity to Washington D. C, Baltimore and Philadelphia make it an easy visit for a weekend or weeklong getaway, where there’s plenty to see and do by day and by night.

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Gene and Katie Hamilton travel the U.S. extensively in search of a favorite place. They are members of the Outdoor Writers Association of America.