Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Discover Oakham’s historic charm with this private pub walking tour, featuring visits to centuries-old pubs, a castle, churches, and a brewery, with included drinks.

If you’re after a way to combine history, local culture, and a bit of fun, the Oakham Private Historical Pub Walking Tour offers a delightful mix of all three. This tour isn’t just about sampling drinks—it’s a journey through one of England’s most captivating market towns, featuring ancient pubs, historic landmarks, and insider stories from knowledgeable guides. It’s tailored for those who want to experience Oakham authentically, without the crowds or cookie-cutter tourist spots.
One standout feature of this tour is the inclusion of a free drink at each pub, which helps you relax and soak in the atmosphere without worrying about the bill. The tour is private, making it perfect for small groups or families wanting a personalized experience. Keep in mind, it lasts around 3 to 4 hours, so it’s a great way to spend an afternoon or early evening. However, if you’re not a fan of walking or have mobility constraints, it’s worth noting that most stops are quite close together, and the pace is leisurely.
A potential consideration is that this tour is focused on Oakham’s historic sites and pubs—so if you’re looking for a more extensive sightseeing adventure beyond the town, you might want to supplement it with other activities. Also, while the price of around $89.54 per person includes drinks and entry fees, you’ll need to budget if you want extra snacks or additional beverages beyond what’s included.
This experience appeals most to history buffs, pub lovers, and those wanting a relaxed, intimate way to explore Oakham. It’s particularly suitable for travelers staying nearby or arriving by train, thanks to its convenient start outside Oakham Railway Station. If you enjoy stories behind buildings and local spots with character, this tour offers a wonderful slice of Rutland life.

Looking for more options in Leicester? Here are some other experiences worth considering.
The tour kicks off at the iconic Oakham Castle, which is believed to be quite unique among English castles. With just a 10-minute visit included, you’ll get a quick glimpse of its well-preserved medieval architecture. The castle’s ancient court and the famous Rutland Stallings—mighty wooden canopies—are among the highlights. The admission is included, so you won’t pay extra, and the guide likely shares stories about its history and the local Lords of the Manor.
Next, it’s just a short 3-minute walk to the Wheatsheaf, an atmospheric old pub that’s perfect for your first drink. It’s a place where history seeps through its walls, and the cozy ambiance makes it easy to settle in. The tour includes a drink here, giving you a chance to savor local ales or ciders in a friendly setting.
A highlight for many visitors is the majestic Grade I listed church whose spire can be seen from miles away. While it’s a brief stop (around 10 minutes), the church’s architecture and history are worth noting. It’s a striking visual reminder of Oakham’s past prominence and religious heritage.
Next, you’ll visit the bustling Market Place, home to the old Buttermarket and Stocks. The Stocks are a quirky, nostalgic relic of bygone punishments, and the Butter Cross adds a picturesque touch to the square. These are free stops but rich in story—the guide might share amusing or startling tales about public punishment and local commerce from centuries past.
One of the most atmospheric stops is The Admiral Hornblower, an old pub set in a rustic building. It’s well-known for its food and drink, but what visitors really appreciate is its ambiance—a perfect spot to relax, chat, and enjoy your included beverage. The guide’s anecdotes about the pub’s history and its role in local life make it a memorable stop.
In April 2024, Oakham unveiled a new statue of Queen Elizabeth II, and this tour gives you a chance to see it firsthand. The statue, featuring the Queen and her beloved corgis, has gained local attention, and it’s a fun photo opportunity. It’s a quick 5-minute stop but adds a contemporary touch to the tour’s historical focus.
The tour wraps up at the award-winning Grainstore Brewery, which is right next to the station. Here, you’ll enjoy an additional 30-minute visit to sample some of Oakham’s own brews. This brewery is a source of local pride, and the taproom offers a fantastic range of drinks, making it a fitting end to your exploration of the town. The inclusion of this stop really highlights Oakham’s brewing heritage.
Finally, the tour visits The Captain Noel Newton, a Wetherspoon pub with its own interesting history and character. Once again, your included drink here caps off the experience, and most reviews note the pub’s friendly atmosphere and interesting interior features.

At $89.54 per person, this tour offers quite a bit of value. The cost covers all entry fees to sites like Oakham Castle, the guided commentary, and a free drink at each pub, which can add up if you’re a frequent pub-goer. The private setting means you aren’t part of a massive group, allowing for personalized storytelling and more relaxed pacing.
While snacks aren’t included, the focus on drinks and local stops makes this a leisurely social outing rather than a food-focused tour. The length—about 3 to 4 hours—strikes a good balance, providing enough time to soak in the sights without feeling rushed.
Reviews note that guides like Stephen are especially well-versed and personable, adding charm and depth to the tour. The anecdotes about lesser-known facts and the stories behind each site make the experience memorable. The atmosphere is relaxed, making it ideal for a casual day out with friends or family.
Starting outside Oakham Railway Station makes the tour accessible for day-trippers from London, Nottingham, Peterborough, and Leicester. If you’re staying in Oakham or nearby, the guide can meet you at your hotel, adding flexibility. The short walking distances between stops mean it’s suitable for most ages and fitness levels.

This tour suits travelers who appreciate history and architecture but prefer a relaxed, social atmosphere. It’s ideal for small groups or couples looking for an authentic local experience without the heft of a large tour. Those who enjoy good stories, charming pubs, and local breweries will find it particularly enjoyable. It’s also a great choice if you want a flexible, private experience that’s easy to fit into a day.

The Oakham Private Historical Pub Walking Tour offers a compelling mix of history, local charm, and social fun. The inclusion of drinks at each stop, coupled with knowledgeable guides, makes it a standout way to explore Oakham’s character and heritage. Whether you’re a history enthusiast, a pub lover, or simply seeking a laid-back way to experience rural England, this tour provides genuine value and a memorable day out.
The tour’s emphasis on authentic sites like Oakham Castle, the historic church, and the beloved local pubs ensures that you’re not just ticking boxes but truly soaking in the town’s spirit. It’s a perfect blend of education, entertainment, and relaxation—an experience that captures the essence of Oakham.

Is this tour suitable for all ages?
Yes, most travelers can participate, and the pace is relaxed enough for a wide range of ages. It’s especially good for adults interested in history and local culture.
Where does the tour start and end?
It usually begins outside Oakham Railway Station and ends back at the same location, making it very convenient for travelers arriving by train.
How long does the tour last?
The tour typically lasts between 3 to 4 hours, giving you plenty of time to explore without feeling rushed.
Are drinks included?
Yes, each person gets a free beer, ale, cider, or soft drink at every pub stop.
Can I customize the tour?
Since it’s a private tour, you can likely communicate your preferences directly with the provider for a more tailored experience.
What sites are visited during the tour?
Highlights include Oakham Castle, Wheatsheaf pub, the historic church, Market Place, Butter Cross, The Admiral Hornblower pub, the Queen Elizabeth II statue, Grainstore Brewery, and Wetherspoon pub.
Is transportation provided?
No specific transportation is mentioned, but stops are within walking distance, and the meeting point is easily accessible.
Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours before the tour, allowing for flexibility.
What is the price?
The cost is approximately $89.54 per person, which includes all entry fees and drinks.
Is this experience family-friendly?
It’s suitable for most adults, but children may need to be comfortable with walking and drinking policies (soft drinks are available).
To sum it up, the Oakham Private Historical Pub Walking Tour is an excellent way to taste the town’s history, architecture, and pub culture in one relaxed, engaging package. It’s perfect for those who love storytelling, local brews, and discovering hidden gems in a friendly, intimate setting.