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304 North Cardinal St.
Dorchester Center, MA 02124

Discover Chester’s medieval past with this 1.5-hour guided walking tour, featuring costumed guides, city walls, Chester Rows, and Roman ruins for just $16.52.
A vibrant glimpse into Chester’s medieval history, the Medieval Walking Tour of Chester offers a lively and engaging exploration of the city’s past. For $16.52 per person, this approximately 1 hour 30 minutes tour takes visitors through key historic sites like the city walls, Chester Rows, and Roman amphitheatre, all led by a costumed guide who brings history vividly to life. The tour is perfect for those interested in history and storytelling, and it is especially valued for its small-group setting, which ensures a more personal and interactive experience.
This guided walk is highly recommended by 97% of participants, and it maintains a perfect 5.0/5 rating based on 141 reviews. It’s a well-priced, accessible option that combines entertainment, education, and walking—making it a compelling choice for visitors seeking to deepen their understanding of Chester’s medieval stories without the expense or hassle of a self-guided tour.

The tour begins at 52 Northgate Street in Chester, a location that is easy to find and close to public transportation. The guide greets guests in medieval attire, immediately setting the tone for an immersive experience. The walk starts with a section of Chester’s city walls, where the guide explains the origins and development of these fortifications, providing a tangible connection to medieval defensive architecture.
Participants are encouraged to appreciate how the walls shaped Chester’s history, especially during times of conflict and rebellion. The walk along the walls offers great views of the city and insight into how they protected Chester for centuries.
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One of the standout features of this tour is the visit to the Chester Rows—the city’s iconic covered shopping galleries dating back to medieval times. The guide walks visitors through these distinctive structures, explaining their original purpose and how they functioned as bustling trade centers.
The 15-minute exploration of the Rows is free of charge but packed with fascinating history. Watching how the shops are layered one above the other paints a vivid picture of medieval commerce. This stop offers a rare glimpse into daily life in historic Chester and the architecture of the period.
Next, the tour visits the Roman Amphitheatre, where the guide describes how the area was used in medieval times. Visitors learn about the significance of the amphitheatre, which originally accommodated public spectacles during Roman rule, and how later, the space was repurposed by St. Johns Cathedral.
This 5-minute stop is free and provides insight into Chester’s layered history—from Roman origins to medieval adaptations—highlighting the city’s rich archaeological heritage.

A key feature that sets this tour apart is the guide’s costume and storytelling style. Guides like Thomas, Richard, and Edward are praised for their enthusiasm, knowledge, and authentic costumes, which include medieval armor and weaponry.
The guides use role-play and humor to explain historical events such as the Hotspur rebellion and the Chester archers’ reputation. This method makes medieval history accessible and engaging, especially for those who might find traditional tours too dry or static.
The tour culminates with an explanation of Hotspurs rebellion, a significant event in Chester’s medieval history. The guide discusses how local conflicts and battles shaped the city, often illustrating these stories through role-play that keeps guests captivated.
The battle of Shrewsbury, explained near the end of the tour, connects Chester’s history to broader historical conflicts, giving visitors a sense of the city’s strategic importance.
The 1 hour 30-minute walk is designed to balance information and movement. The small group size, limited to 15 people, ensures that guides can interact closely with each participant and answer questions. Some reviews mention that the guide sometimes spends more time on storytelling, which may slightly limit the number of sites seen, but overall, the pacing is well received.
The tour is suitable for individuals with moderate physical fitness, as it involves walking along city walls, through streets, and around historical sites. The tour is near public transportation, making it accessible for most visitors.
Participants are advised to meet at 52 Northgate Street; the tour concludes near 19 City Walls by the river near Handbridge. The mobile ticket system streamlines access, and service animals are allowed.

Priced at just $16.52 per person, this tour offers excellent value considering the quality of storytelling, the authenticity of guides’ costumes, and the depth of historical insight. It is booked on average 15 days in advance, reflecting its popularity.
The tour provides a combination of history, fun, and storytelling, making it ideal for history buffs, families, and casual visitors alike. Cancellation is free up to 24 hours before, adding flexibility for last-minute plans.
Reviews consistently praise the knowledge and enthusiasm of guides such as Thomas, Richard, and Edward. Guests appreciate the authentic costumes, role-play storytelling, and ability to bring medieval Chester to life.
Some mention that the tour may spend more time talking than sightseeing, but the entertaining style and depth of content compensate for this. The small-group format and engaging narration make this a memorable experience.
This tour appeals most to history enthusiasts, families with children, and anyone interested in medieval stories, rebel conflicts, and Roman heritage. The costumed guides and interactive storytelling create an immersive atmosphere that makes history exciting and accessible.
Visitors who prefer more extensive sightseeing or architectural details may find the tour somewhat focused on stories and events rather than a comprehensive architectural tour. However, those looking for an engaging, well-presented overview will find this experience very rewarding.
“Very interesting experience. Richard was very knowledgeable about medieval times and the wars that the Chester Longbow men fought. Full of facts an…”
How long is the Medieval Walking Tour of Chester?
The tour lasts approximately 1 hour 30 minutes, covering key medieval sites and stories.
What is the tour price?
The tour costs $16.52 per person, providing excellent value for the storytelling and site visits included.
Where does the tour start and end?
It starts at 52 Northgate Street and ends near 19 City Walls, by the river close to Handbridge.
Are guides dressed in costumes?
Yes, guides wear medieval costumes, enhancing the immersive storytelling experience.
Is the tour suitable for all fitness levels?
The tour requires moderate physical activity, mainly walking and standing, suitable for most people with average fitness.
What sites are included in the tour?
Key stops include the Chester city walls, Chester Rows, and Roman amphitheatre.
Can I cancel the tour if my plans change?
Yes, free cancellation is available up to 24 hours before the tour start time.
Is this tour good for children?
Yes, the engaging storytelling and costumes make it enjoyable for children and adults alike.
This Medieval Walking Tour of Chester offers a lively, informative journey through the city’s past, led by passionate guides in authentic costume. With its great value, focused stops, and interactive approach, it stands out as a top choice for anyone eager to bring Chester’s medieval history to life.