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Top 30 Destinations by Personality Type
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Chester, England

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Did You Know … ?

  • Chester is the only city in Britain that maintains the tradition of a regular midday town crier.
  • One shop in Chester Rows is believed to have Britain’s oldest surviving storefront (c.1200).
  • The Romans used Cheshire Cheese in cheese-rolling contests.
  • Chester is the only British city that retains the full circuit of its defensive walls, two miles’ worth.
  • The Chester Regatta is the world’s oldest rowing competition (1733).

Of centurions, cats and cheese

Chester is generally not in the top tier of English cities that North Americans put on their must-see lists, but when they finally give Chester a look, most are not disappointed. In fact, they are likely to trumpet the small city — with its remarkably intact historic walls; its collection of distinctive architecture, and a real-live town crier — as their own personal discovery.

From its founding (79 A.D.), Chester, which is quite near England’s border with Wales, was an important Roman military outpost. By great good fortune, today it boasts major evidence of that Roman history, particularly in its amphitheater, the largest unearthed in Britain. Even the city walls include some Roman sections. Chester takes advantage of this — and entertains its visitors — with tours led by “Roman soldiers.”

Other notable sights are a cathedral with Norman origins; medieval construction which includes parts of the city’s defensive walls; irresistible mock-Tudor buildings, and Victorian contributions including the striking town hall. The Grosvenor Museum and the Cheshire Military Museum tell part of the Chester story, too.

The city seems made for history buffs, but it is too limiting to stop the discussion there. Chester’s bragging rights extend to the River Dee and Shropshire Union canal which provide touristic fun on the water; a popular racecourse in the middle of town, and floral drama in gardens in and near the city — not to mention the shopping in a medieval “mall,” meaning Chester Rows.

The gardens include those at Eaton Hall, the family home of the Duke and Duchess of Westminster, south of Chester. The gardens and some rooms are opened to the public four times a year for charitable fundraising.

Finally, the city sits in Cheshire, the county that gave its name to a smiling cat, but first it gave its name to a cheese. Evidence suggests the Romans brought cheese making to the area via Chester. Even if that is not so, a cheese with roots in the Chester area has been around since Roman times.

Things to do for Venturers

  • Hear pop and rock stars at the two-day outdoor music festival called Chester Rocks. The July event takes place in the Chester Racecourse.
  • Join a nighttime ghost tour then brace yourself for dark truths — and a few tall tales.
  • Download a narrated tour to your iPod, mobile phone or other device, then walk to the city’s main sights at your own pace.
  • Time your visit for the summertime Cholmondeley Pageant of Power, a showcase for historic and contemporary automotive power as applied on land, sea or in the air. See cars and bikes in competition; motorized boats and aircraft also display their power.
  • Get out of town for a hiking trip. Tackle the 35-mile Gritstone Trail, or some part of it. It is at Macclesfield east of Chester.
  • Attend a cooking workshop at the springtime Chester Food, Drink and Lifestyle Festival. Stick around for one of the event’s evening BeerFests or spend the weekend at the racecourse for CamperFest.

Things to do for Centrics

  • Hire a boat for the day and cruise on the Shropshire Union canal between Christleton, just outside Chester, and Beeston. The purpose-built narrowboats accommodate up to eight.
  • Walk around the oldest part of town, literally, by walking atop the entire circuit of the city’s nearly two miles of walls.
  • One walking tour is meant to tempt the foodie in you. Called A Taste of Chester, the tour weaves Chester’s 2,000-year-old story around food-tasting experiences. Buy Cheshire cheese.
  • Head to the racetrack, which is in the middle of town, to see the horses in action.
  • And go horseback riding. Take lessons, too, if you need them.
  • Overnight at the historic Bear and Billet and sample the ales in its pub. Then, shop in the Chester Rows, a set of two-tiered enclosed shopping galleries. The Three Old Arches building dates from the 13th century; some others are Victorian copies of medieval half-timbered buildings.

Things to do for Authentics

  • Take a walking tour led by a Roman soldier (well, someone dressed like a Roman soldier). You will see the amphitheater and other sites associated with the city’s earliest days.
  • Take a sightseeing cruise on the River Dee, which runs through the city.
  • If you are in town on a summer weekend, listen for the free entertainment emanating from the city’s 19th century bandstand.
  • Plot your strolls around town to be near the town’s High Cross when the town crier calls out the news or reassurances that all is well.
  • Surviving walls and other structures tell something of the Chester story, but fill in some of the gaps at the Grosvenor Museum and the Cheshire Military Museum.
  • See the ornamental gardens and romantic exterior of the Cholmondeley Castle. Carry and enjoy your lunch at a lakeside picnic area on the grounds.

Additional Resources

For more information, consult Visit Chester at