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Explore Oakham on a Private Walking Tour - Book Your Oakham Walking Experience

Discover the thousand-year history of Oakham on a private walking tour that lets you explore every corner of this beautiful, vibrant market town and county town of Rutland; you’ll wander the old walls and see the unique Oakham Castle set beside its lovely park and historic old bandstand, admire the fabulous old church, and spot the traditional Stocks in the Buttermarket, all at your own pace and on your schedule, making it ideal for a day out or a longer stay away from the noisy chaos of London; food lovers will enjoy exploring local tastes and markets, and please note that the museum and castle interior are closed on Sundays and Tuesdays.

About this activity in Leicester City Centre

Cancellation policy
For a full refund, cancel at least 24 hours before the scheduled departure time.

Highlights

  • Explore historic Oakham on a private walking tour that traces more than a thousand years of local heritage in Rutland.
  • Enjoy a tailored itinerary that reveals hidden corners - from the castle and its surrounding park to the old bandstand and medieval church.
  • See quirky local features such as the Buttermarket and the historic stocks while sampling the town’s vibrant food and artisan scene.
  • Take the tour at your preferred pace and time - it’s just for you, ideal for day trips or as an orientation for a longer stay in the area.

Important Information

  • This is a private walking tour of Oakham in Rutland; it includes any required entrance fees for sites visited.
  • The town is compact and easy to navigate, suitable for all fitness levels; routes accommodate wheelchairs and prams, and service animals are welcome.
  • Public transport connects to the town centre and accessible transport options are available nearby for arrival and departure.
  • Please note the museum and the interior of Oakham Castle are closed on Sundays and Tuesdays - plan visits to interiors on other days.

Meeting Point

Meet in Oakham town centre by the entrance to Oakham Castle near the Market Place; your guide will be waiting to start the private walking tour.

Includes

  • You’ll enjoy a private walking tour in Leicester City Centre as part of your booking
  • Any entrance fees are included so you can focus on exploring the area

Other

  • The experience is wheelchair accessible in Leicester City Centre, with accessible routes for easy navigation
  • You can bring infants and small children - prams or strollers are suitable for use here
  • Service animals are allowed, so you can travel with trained companions
  • Public transportation options are available nearby to help you reach the meeting point and surrounding attractions
  • Transportation options in the area are wheelchair accessible to support accessible transfers
  • The activity is suitable for all physical fitness levels, making it a good choice for mixed-ability groups

Customer Reviews

10/10
Based on 2 Reviews
W8338RPemilyb
• May 7, 2025 04:09:01 PM
Summary: A fabulous tour around Oakham with Stephen . Highly knowledgeable, personable and with an excellent sense of humour ! We saw fascinating artefacts , unique buildings and heard lots of fun stories about Oakham including the smallest man from the smallest county . We loved the 5 legged stocks and the statue of the Queen with her corgis ! This is a must see tour and Stephen is fabulous
359pjp
• Apr 1, 2025 11:58:21 AM
Summary: An excellent tour, full of fascinating facts presented in a friendly and relaxed style. Stephen clearly researched his subject very thoroughly and is very knowledgeable. This combined with his style of delivery and enjoyable company made for a most enjoyable morning spent in this delightful English country town.

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Know more about Leicester City Centre

Oakham is a beautiful, vibrant market town with over a thousand years of history that feels wonderfully calm compared to London. It makes an ideal day out or long weekend destination where you can stroll historic streets, relax in the park by the castle and discover local food and shopping.
Yes - the tour is private, just for you, and runs when you want it and at whatever pace you like, making it easy to tailor the experience whether you’re getting your bearings or seeing everything in one visit.
No - please note the museum and castle interior are closed on Sundays and Tuesdays, so plan your visit or tour accordingly to avoid disappointment.
The private walking tour explores the town’s nooks and crannies, including the unique castle set within its old walls and park with the bandstand, the fabulous old church, the historic Stocks in the Buttermarket, and other highlights around the market town.
Absolutely - Oakham and Rutland are known for being great for foodies, with lots to see and buy locally. The tour gives you a chance to sample local fare and explore market stalls and independent food offerings in the town.
Yes - the private format and relaxed pace make the tour well suited to families, couples, groups and people looking for tours and sightseeing, whether you’re visiting for a day out or a longer stay in the market town.