PHOTO: The Chester Cathedral’s origins date back to 1092. All photos courtesy VisitBritain.

For American tourists, Chester (www.visitchester.com) has most frequently been enjoyed as a day trip out of Liverpool or Manchester. It works well that way but, at the same time, it almost seems like that approach sells Chester short. It was, at one-time, an important Roman outpost and a secondary capital for England’s tragic King Richard II. Chester, whence comes Sir Gawain and the Green Knight, is the best repository for the richness of the art, literature and history of medieval England northwest of York. In medieval grandeur and majesty, York Cathedral is peerless in the U.K., but Chester has a charm that, in my view, surpasses even the great York.

The town’s two-tier shopping galleries called The Rows, were created about 700 years ago, and they give the city a signature look of black half-timbered buildings two stories high. In Chester, they promote The Rows as a retail shopping mecca as “two high streets-in-one.” The Rows in Chester constitute several complexes of Tudor, half-timbered buildings joined by long galleries. They date back to the 13th century as venues for shops and warehouses at street level, with long galleries above the street.

The Mad Hatter’s Tearoom is located on Bridge Street Row. Dating from the 13th century, Mad Hatter’s offers a menu of locally sourced homemade dishes, which includes light lunches and the city’s best-known afternoon tea. Their cupcake tower is known for its huge variety of flavors. It also offers cupcake-decorating classes.

PHOTO: The town’s black half-timbered buildings give Chester a signature look.

A Centurion Stroll

Roman centurions in full and authentic dress leading groups are a common sight in Chester. The very name “Chester” comes from the Latin for “fortress.” For the Romans this site was a very large and important military complex. It had to check any advance by the “Wild Welsh” just across the border. How wild were the Welsh? One of the most prominent tribes was the Brigantes, a word that made its way into our language as “brigands.” In antiquity this area was a wilderness of tribal warfare, and that military edge stayed with the city all the way through the English Civil War, when Chester was under siege for two years.

While guides in period clothing are a turn-off for many travelers, in Chester these faux centurion guides are so informed and the uniforms they wear so accurately recreated, that the apparent silliness of it diminishes quickly. As is often the case in the U.K., the guides are so well informed that any sense of cheesiness is eradicated by their command of history. Chester’s Roman amphitheater is said to be Britain’s largest, and the 2005 excavation gathered much of what you’ll see at the Grosvenor Museum.

The Roman amphitheater and Chester Cathedral preserve two vastly different historical epochs in the city’s long life. Chester Cathedral escaped the destruction that most British cathedrals faced during the Reformation, when the Tudors were driving Catholicism out of the country. Thank goodness it survived.

Intimate Cathedral

The Chester Cathedral’s origins date back to the foundations of a Benedictine monastery in 1092. The paradoxical combination of the cathedral’s intimate scale and yet soaring grandeur probably stems from its monastic origins and its passage through a Romanesque phase before going grand in the age of Gothic cathedrals. It’s believed that a Roman Temple to Apollo was the original religious building on the site. Throughout the Romanesque portions of the building, fragments of Roman architecture (especially columns) can be found in the construction.

The ramparts on the Chester City Walls (www.explorethewalls.com) offer a great two-mile walk. The walls were begun as a dirt mound encircling the old Roman encampment of the town they called Deva. The walls evolved over the centuries until they became what they are today. In the 18th century the walls evolved into an area for strolling, much like New York City’s High Line. Don’t let that relaxing atmosphere fool you—these walls served to protect Chester from attacks during Roman times, the Norman Conquest and, lastly, during the English Civil War.

PHOTO: The ramparts on the Chester City Walls offer a great two-mile walk.

There are times when you can watch races at Chester’s Racecourse, the oldest in Britain, from the city walls. Horse racing has been a staple in Chester for almost five centuries. The first race took place in 1539. Located along the River Dee, the race track’s infield is centered by a cross, giving the course the nick name “Roodee.” “Rood” is the Anglo Saxon name for cross. The White Horse (www.thewhitehorsechester.co.uk), a restaurant and pub that opened last year at the course, offers day-long packages for those wanting to dine and imbibe from a great seat at the track. In 1903 the infield was used by Buffalo Bill for his Wild West Show.

Buffalo Bill would have loved the shark encounter at Chester’s Blue Planet Aquarium (www.blueplanetaquarium.com). Shark dives are offered on Friday, Saturday and Sunday at 2.15 p.m. or 4.15 p.m. The aquarium’s shark encounter program has been so successful that it’s used for the occasional wedding ceremony in the tank. Even beginners can get up close and personal with the collection of 10-foot Sand Tiger Sharks. Though the species is large and ferocious looking, they have little or no record of attacking humans. Beginners will be taught basic dive techniques before being lowered into the tank with the sharks.

Visit Chester offers a 90-minute walking tour at 2 p.m. on Sundays, Mondays and Tuesdays known as Secret Chester, which is led by guides who have keys to places rarely open to the public. There are three different routes, and so the tour could include medieval wall paintings in a Norman castle tower, one of the few remaining cameras obscura in the country, a Water Tower, with no water or the King Charles’ Tower, which mixes medieval architecture with a Civil War story and more.

Chester is a member of an eight-city joint marketing effort entitled Britain’s Heritage Cities (www.heritagecities.com). The organization is great for creating itineraries that combine the various member cities according to theme. The other cities are Bath, Brighton, Durham, Stratford-upon-Avon, Oxford and York. The Christian Heritage itinerary covers such Christian touchstones as C.S. Lewis, the Pilgrim Fathers, York Minster and the Chester Mystery Plays. The Christian itinerary is just one of eight; other programs include Houses and Gardens; Literary, Visual and Performing Arts; Great Castles, Stately Homes and Gardens in England¹s North Country; Great Cathedrals of England¹s North Country; Great Gardens of England¹s North Country; to name a few.