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304 North Cardinal St.
Dorchester Center, MA 02124

Discover Oakham's history and charming pubs on this private 3-4 hour walking tour, including drinks, visits to historic sites, and a visit to a local brewery.
Explore the Oakham Private Historical Pub Walking Tour, priced at $89.54 per person, offering an engaging blend of history, local pubs, and scenic sights in the heart of Leicester, England. With a duration of approximately 3 to 4 hours, this private group experience combines cultural stops with refreshing drinks and storytelling led by a knowledgeable guide. The tour starts at Oakham Railway Station, making it a convenient outing for day-trippers from London, Nottingham, Peterborough, or Leicester, and it’s equally suited for visitors staying at local hotels in Rutland or Oakham itself.
This tour stands out for its in-depth visits to some of Oakham’s most historic sites, including Oakham Castle and the Grade I listed church, along with stops at some of the town’s most characterful pubs. The inclusion of a free drink at each pub enhances the experience, as does the visit to Oakham’s own brewery, ensuring a satisfying blend of history, architecture, and local flavor. While the tour is not focused on food, soft drinks are available, and the informative commentary makes it an ideal choice for those interested in local history and traditional pub culture.


The tour begins conveniently outside Oakham Railway Station, a perfect meeting spot for those arriving from London, Nottingham, Peterborough, or Leicester. The accessible location makes it straightforward for day-trippers and visitors staying nearby. If staying in Oakham or Rutland, the guide can meet guests at their hotel, ensuring flexibility.
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The first stop is at Oakham Castle, an attraction that might be unique in its preservation and charm. The tour includes 10 minutes at this site, where the admission ticket is included. Visitors appreciate the opportunity to see a historic castle structure that offers a glimpse into medieval architecture. The guide shares stories about the castle’s significance and its distinctive horseman’s heads, which are a notable feature.

Next, the tour makes a short 3-minute walk to the Wheatsheaf pub, an old and beautiful pub that provides a cozy setting for a drink. The admission ticket for this pub is included, and guests can enjoy a refreshing beverage in an atmosphere filled with character and history. The pub’s rustic charm offers a perfect spot to soak in Oakham’s pub culture.

One of the tour’s highlights is the impressive Grade I listed church, whose spire is visible from miles away. Visitors get to admire the architectural beauty and learn about the church’s historical significance. The stop here provides a moment of reflection amid the bustling town, with free access and the chance to appreciate the medieval craftsmanship.

A 10-minute stop at the Market Place offers a look at the Buttermarket and stocks, which are reminders of old public punishment practices. The free stop allows for some photos and a chance to imagine the lively marketplace that has served Oakham for generations. The stocks stand as a tangible link to the town’s past.

Just nearby, the Butter Cross and Stocks are visible for another 10 minutes. This spot underscores Oakham’s historic market traditions and provides an opportunity for visitors to observe public punishment relics. The free stop complements the tour’s theme of exploring the town’s public and social history.

The tour’s midpoint is at The Admiral Hornblower, a rustic and atmospheric pub renowned for great food and drinks. Set in a beautiful building, this 30-minute stop allows guests to enjoy their included drink with stories about the pub’s history and local reputation. The ambiance and character make it a memorable part of the journey.

A brief 5-minute stop features the statue of Queen Elizabeth II, unveiled in April 2024. This memorial was the first and only statue of the late Queen in Oakham, making it a recent addition to the town’s landscape. Visitors appreciate the personal touch of the Corgis, which many find charming.
The tour wraps up at the Grainstore Brewery & Tap, an award-winning brewery located right next to Oakham station. This 30-minute visit includes a range of drinks from Oakham’s very own brewery, providing an authentic taste of local brewing craftsmanship. It’s a fitting way to end the experience, especially since it’s located conveniently at the tour’s start and finish point.
The last stop is at The Captain Noel Newton, part of JD Wetherspoon. This pub is regarded as potentially the best Wetherspoon’s in the area, with interesting history inside. The 30-minute visit allows guests to relax, enjoy their final included drink, and soak in the lively pub atmosphere.
The tour includes a free drink or soft drink at each pub, making the experience friendly for those who prefer non-alcoholic options. The tour is private, ensuring a personalized experience with only your group participating. Confirmation is received within 48 hours and free cancellation is available up to 24 hours in advance, providing flexibility.
This experience is ideal for history enthusiasts, pub lovers, and those seeking a relaxing way to explore Oakham’s historic architecture and local culture. It suits visitors who want a structured yet intimate tour with included drinks and a guided storytelling style. The pace is moderate, and accessibility is considered, with most travelers able to participate.
This tour offers an authentic taste of Oakham’s history, paired with visits to some of the town’s most charming pubs and historic sites. The inclusion of drinks at each pub enhances the convivial atmosphere, while the stops at Oakham Castle, the listed church, and the Queen’s statue provide cultural depth. It’s a thoughtfully curated experience that balances entertainment, education, and relaxation.
While not focused on food, the drinks and engaging guide make this a pleasurable outing for those interested in local history and pub culture. It’s well-suited for groups and individual travelers alike, especially those wanting a private and flexible way to discover Oakham’s stories.
“Stephen is extremely well versed in all things historical and is also very personable. We had a fun tour around town visiting four pubs with a dri…”
Is the tour suitable for children or families?
The tour is designed for most travelers and involves walking and pub visits, so it can be suitable for families, though minors should be aware of the alcohol consumption at stops.
Can I participate if I don’t drink alcohol?
Yes, soft drinks are available as an alternative at each pub, and the tour can accommodate those who prefer non-alcoholic options.
How long does the entire tour last?
The tour lasts approximately 3 to 4 hours, with most stops lasting between 5 and 30 minutes, depending on the site.
Where does the tour end?
The tour concludes at Oakham’s Grainstore Brewery & Tap, located next to the station, making it easy to continue exploring or catch a train.
What’s included in the price?
The price includes admission tickets, a drink at each pub, and the guiding service. Snacks are not included.