For most visitors, Chestertown conjures images of colonial architecture, river views and trendy shops. But Kent County's seat reminds me of Spider-Man, tuna melts and Bubba Jenny.

Gliding across the Chester River Bridge and into this Eastern Shore town's compact center will always evoke memories of weekly visits with my great-grandmother.

The setting was McCrory's, the old five-and-dime on High Street. Jeanette Fox was stooped with age but her hazel eyes were still bright during Saturday lunches 20 years ago. After a meal of drippy sandwiches in the luncheonette, she would gossip with our mother while my sister and I spent the dollar she gave us on comics and candy.

I didn't know much about the town's history. Rather than discover that Chestertown once rivaled the ports on the western shore or that George Washington had served for five years on the board of Washington College, I was more interested in my great-grandmother's personal narratives. However, I have since come to realize that Chestertown has much to offer beyond the walls of the five-and-dime.

Historic: High Street is home to beautiful architecture thanks to Chestertown's past as a busy port. (Sun photo by Chiaki Kawajiri)

Port to riches

To begin to uncover Chestertown's colonial past, head downtown to the Geddes-Piper House, tucked between Maple Avenue and High Street. This 1784 townhouse is the home of the Historical Society of Kent County and allows visitors a look inside one of these colonial-era beauties. Its collection of 18th-century furnishings, antique maps of the region and cooking implements give a good overview of the town's beginnings.

Founded in 1706, Chestertown rose in stature when it was named one of the colony's six Royal Ports of Entry. The shipping boom that followed this designation made the town at the navigable head of the Chester River wealthy. In the mid-18th century, Chestertown trailed only Annapolis as Maryland's leading port.

A burgeoning merchant class infused riches into the town, reflected in the many brick mansions and townhouses that sprung up along the watefront. Another area in which Chestertown is second only to Annapolis is in its number of existing 18th century homes.

Like Donald Trump in this century, William Geddes put his name on homes (the Geddes-Piper House) and ships (the brigantine Geddes). It was this ship that local tax rebels rowed out to on May 23, 1774 to toss its cargo of tea into the river, five months after a similar "tea party" in Boston.

Chestertown's Tea Party Festival, held every Memorial Day weekend, commemorates this event and invariably includes a few guys in tricornered hats getting plunked into the river. It's the town's biggest weekend of the year as tourists cram the streets strolling among booths filled with crafts and food.

The newest addition to Chestertown's maritime history is the schooner Sultana, whose homeport is a dock at the end of Cannon Street. Built largely by local volunteers and launched last year, the Sultana is a reproduction of a 1768 ship that served in the British Royal Navy. In addition to running educational tours for area schoolchildren, the Sultana offers public sails throughout the spring and summer months to give visitors a taste of the salty life.

To the manor born

More examples of Chestertown's colonial architecture may be found at the watery end of town. The aptly named Widehall, at the corner of High and Water streets, is a 1770 Georgian home built by Thomas Smythe. Smythe was a merchant who is believed to have been one of the area's richest citizens. His wealth is reflected in the home's use of the "header bond" technique of construction, whereby bricks are laid with their short ends out. This method required twice as many bricks to build the walls. A gaze at Widehall's river side reveals gabled porches, ionic columns and a widow's walk, all before a stately green lawn that rolls to the Shore.

Knowledge: The Casey Academic Center on the campus of Washington College. (Sun photo by Chiaki Kawajiri)

Farther down Water Street is the 18th century Hynson-Ringgold House, home to Washington College presidents since 1944. Baltimore art fans may already be familiar with some of its interior. The finely carved woodwork and King of Prussia marble hearth of its east room were moved to the Baltimore Museum of Art in 1932 and can still be viewed there.

More of Washington College is housed across the street at the 1746 Custom House. This is where William Geddes worked as the custom collector until his tea -- and eventually, the whole colony -- was tossed into the revolution. Today it holds the C.V. Starr Center for the Study of the American Experience, a branch of the small, liberal arts college whose main campus is located at the other end of town.

W.C. and G.W.

Washington College's main claims to fame are its age -- founded in 1782, it is the nation's 10th oldest college -- and its link to its namesake, George Washington. It is the only school the first president himself authorized to use his name. He also put his money where his surname was, giving the school 50 gold guineas to help start its endowment.

The school's nearly 1,000 undergraduates live and study in a group of colonial and colonial-style brick buildings around a pretty, green quad on Washington Avenue. In the spring, men's lacrosse games are a big draw as Washington College is considered to have one of the best teams among small colleges.

Room and board

In colonial times, Chestertown was near the center of the 13 colonies and became a popular stop on the route to and from Philadelphia. It is no surprise then that Washington also slept here, staying at Worrell's Tavern, which then stood at the corner of Cannon and Queen streets.

Oystermen for a day: Tourists return from two hours of "tonging" for oysters on the Chester River. (Sun photo by Kenenth K. Lam)

For modern-day visitors who wish to stay overnight, the Imperial Hotel offers fine accommodations in its romantic Victorian building on High Street. Its elegant dining room serves gourmet meals such as garlic-smoked quail or pan-seared rockfish with deviled crab.

For afternoon tea, try the White Swan across the street. Restored to look the way it did in 1793, the tavern offers the most authentic colonial dining experience in town.

The Feast of Reason, also on High Street, offers sandwiches that are more upscale than the fare at the old five-and-dime. Try the turkey with tarragon on wheat or a spinach, zucchini and provolone wrap. Enjoy your sandwich al fresco at Fountain Park in the center of town. Saturday mornings from April to Christmas, area farmers offer even more tempting treats by displaying the fruits of their labor.

Foodies will find much to ogle at the Chestertown Cooking Company on High Street. Like a locally owned Williams Sonoma, this shop offers serious cooking implements and classes for amateur cooks.

Shopping center

The two square blocks bounded by Mill and Queen streets to the north and south and High and Cannon streets on either side make up Chestertown's main shopping district. Cross Street -- right in the middle of this grid -- offers a number of charming shops. The Home Gallery has an eclectic collection of wooden furniture and metal watering cans in bright primary colors. Try Twigs & Teacups for gifts from books to compact discs, clothes and cards. Play it Again Sam, across the street, is the place to go for a java-fix beneath a mural depicting a Chestertownie's view of the world (the Chesapeake Bay is almost as big as the Pacific Ocean.)

Not far from nature: Wheat, serving as feed for migratory birds, grows naturally from seeds scattered from nearby fields along the Chester River. (Sun photo by David Hobby)

Scottie's Shoe Store is around the corner. It might not seem it at first glance, but "this is the center of town," according to proprietor Anna Cole.

Surrounded by her merchandise, from work boots to gloves and even penny candy, Cole also does a brisk business selling newspapers. Big city transplants often line up out the door on Sunday mornings for the New York Times, Washington Post and Philadelphia Inquirer -- papers that don't offer home delivery to the largely rural Eastern Shore.

On a recent weekday morning, a steady stream of regulars strolled in to chat, pick up a paper or leave some change on Cole's worn counter. Those with dogs got a handful of treats with their news.

"I'm the best-educated woman in town," Cole says, noting that I have come too late to witness the group of town elders that always gathers to "discuss the world" shortly after the shop opens at 6 a.m.

The only thing missing from Cole's shop is comic books. While both Bubba Jenny and the five-and-dime are gone now, their spirits live on here among the gossip and tales.

As Chestertown prepares to enter its fourth century, its history is now being written under Cole's observant eye.

"I know everything," she says with a wink.

As I'm about to leave, Cole adds one last comment as if to prove her point.

"Don't worry about the parking meters today," she says. "The [metermaid has] gone to Virginia Beach."