More Than Just a Pub Crawl
History, character and great ales — woven through every street and every stop
The Oakham Pub Tour isn’t just a pub tour — it’s one of the finest ways to explore this extraordinary little market town. Between stops we’ll pass the unique Norman castle, discover atmospheric alleyways, see the ancient Buttercross and stocks in the market square, and uncover the kind of local stories that only a guide who actually lives here can tell.
A drink is included in every pub we visit — beer, real ale, cider or soft drink, your choice. Rutland is famed for its extraordinary food and drink, and its pubs are a big part of that reputation. This tour visits five of the finest, each with its own remarkable character and history.
“I have fond memories of the Admiral Hornblower — I stayed there for a few nights during the week of the Queen’s funeral, visiting a dear friend who lived locally. The atmosphere was rather surreal, but this pub and this beautiful little town made such an impression on me that I decided to move here. Well, ten minutes walk away. This tour is my way of sharing what I fell in love with.”
— Stephen, your guide & Oakham resident
The Wheatsheaf — our first stop, a 17th-century gem with oak beams & real ales
The Five Pubs
Five remarkable stops through the heart of Oakham
A lovely 17th-century local — snug, cosy, with oak beams, a beer garden, real ales, whiskies and rums. After walking past the unique Oakham Castle, this is exactly the right place to begin.
Pricing
Per Person — A Drink in Every Pub Included
Beer, real ale, cider, soft drink or hot drink — your choice at every stop. Child prices available on request.
Train fare not included — book via National Rail. Groups of 5–10 very welcome.
Book by email, via Viator, or use the booking calendar below.
Frequently Asked Questions
Starting Time: About Midday… depending on you.City Location: Oakham
Duration of Tour: 3-4 hours Approx
Meeting Point: Oakham Railway Station for those arriving from London (about 40 minutes to Peterborough then 25 to Oakham) or elsewhere. Otherwise we can meet you at your hotel in Oakham or mutually convenient location.
How to book Oakham Private Pub Tour
Standard Adult Prices per person includes a beer, ale, soft drink etc in each pub (child prices available upon request).
1 Adult = £80
2 Adults = £70
3 Adults = £60
4 Adults = £50
5 – 10 Adults = £40
To make a booking please contact us on the button above or use the booking form below.
Or book instantly via Viator below. The Grainstore Brewery Tap is right next to the station — so you can pick up a bottle or two from the shop before catching your train home. Combine with the walking tour for a wonderful full day in Oakham.


