Things to do in Oakham, Rutland: A local’s guide

Visiting Oakham, the county town of Rutland, is a delightful experience that combines history, charm, and a welcoming community. This small but vibrant town offers a mix of historic landmarks, great food, and a lively atmosphere, surrounded by the beautiful Rutland countryside.

At the heart of Oakham is its most famous landmark, Oakham Castle. This historic site is home to a stunning 12th-century Great Hall and a unique collection of decorative horseshoes, a tradition started by visiting royalty and nobility. Nearby, the Rutland County Museum provides a fascinating glimpse into local history, with displays on rural life and the area’s rich heritage.

Oakham’s High Street is filled with independent shops, cafes, and restaurants, perfect for a leisurely browse or a bite to eat. For a memorable meal, Hitchen’s Barn offers modern British dishes made with local ingredients in a cozy yet stylish setting. If you’re in the mood for something more relaxed, head to The Grainstore Brewery, a popular spot for craft beer enthusiasts and a great place to soak up the town’s friendly atmosphere.

With its historic sites, excellent food, and a warm community feel, Oakham is a perfect place to explore – whether you’re visiting for the day or staying to discover all that Rutland has to offer.

Oakham’s History

With a rich history dating back to the Saxon period, Oakham boasts a fascinating past that has left its mark on the town to this day.

One of the most notable landmarks is Oakham Castle, which dates back to the 12th century.

The castle was built by Walkelin de Ferrers, who was the Lord of the Manor of Oakham at the time.

Today, the castle (spoiler: it’s not really a Castle) is open to the public and is home to a fascinating collection of horseshoes, which have been donated by members of the royal family and other notable figures throughout history.

The town’s history is also closely tied to the agricultural industry, which has played an important role in its development over the centuries. From the wool trade to the production of grain and other crops, Oakham has always been a hub of agricultural activity.

Today, Oakham is a popular destination for tourists and history buffs alike, who come to explore its rich heritage and traditional charm.

Things to do in Oakham

Whether you’re visiting for the day, or spending a little longer, there’s plenty of things to do in Oakham. And due to the small size of the town centre, it’s really easy to walk between everything.

It’s also possible to enjoy the many things to do at Rutland Water by foot, by heading to the Library end of the town, and taking the short walk to the nearby village of Egleton.

Head out past the council offices, and walk down Uppingham Road, before crossing the busy A6003.

You’ll soon be at Rutland Water Nature Reserve, which boasts a vast array of wildlife and bird species. There’s a visitor wildlife visitor centre, so you can understand more about the importance of what’s in front of you.

From here, you can also access many of the walking and cycling trails that link to the wider reservoir.

When is a Castle not a Castle? When it’s Oakham Castle, a former Norman stronghold, built in the 12th century! The Castle’s Great Hall is home to hundreds of horseshoes. There’s also tonnes of educational resources here so it’s a popular day out for the family.

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Also packed full of history is Rutland County Museum. Showcasing the agricultural importance of Rutland, there are lots of exhibits on display including many of the giant farming machines that would have worked the land locally.

There’s also a rather ominous gallows and occasionally you can watch films and shows in the purpose built entertainment area.

Other Oakham Attractions

If you’re a foodie, then you’ll want to make sure you visit the popular Oakham Farmers’ Market, which takes place on the third Saturday of every month (except in December).

It pretty much takes over Gaol Street and gives local food producers the chance to sell their produce. It’s hugely popular and a good chance to stock up on artisan bread, locally reared meat, cheese , cakes and vegetables.

There’s also a regular market in Oakham every Wednesday and Saturday.

All Saints’ Church is an iconic landmark and one of the most historic churches in the region. Built in the 14th century, the church boasts impressive architecture, including an octagonal tower and decorative carvings.

Oakham offers a range of attractions and activities for visitors of all ages.

Our favourite things to do in Oakham

• Oakham Castle Horseshoes: Oozing with history. OK, it’s not a castle but it’s pretty impressive. Children will love exploring the horseshoe collection and recognising famous Royals from years gone by. Did you know the Castle is also used once a year as a Magistrates Court? There is a huge amount of ceremony around the court sitting and it’s great to watch the procession outside.
• Explore Rutland County Museum: Opposite the council offices, it’s like stepping back in time to explore Rutland’s history. Exhibits cover archeology, geology, and social history.
• Take a stroll in Cutts Close Park: This beautiful park is located in the heart of Oakham and is perfect for a picnic or a walk, with plenty of wide open space. It also features a playground suitable for younger children, more grown up play equipment, a skatepark, and a pavilion that hosts various events throughout the year.
• All Saints Church: Worth exploring if you appreciate history and particularly churches. It’s pretty impressive from the outside and appears in many an online photo album.
• Oakham School: Founded in the 16th century, the buildings and grounds of this famous school are stunning. There are several sites around the town, and the students regularly hold lunchtime concerts in All Saints Church.
• The Grainstore Brewery: This award-winning brewery is a must-visit for any beer lover. They have an impressive range of local beers, many brewed on site. You can even take a guided tour to learn more about the brewing process.
• Farmers Market: If you’re lucky enough for your trip to coincide with the Farmers’ Market – third Saturday of every month – then it’s well worth visiting. Head to Gaol Street for locally produced meats, cheeses and bread.

Shopping and Events

For those wanting some retail therapy, Oakham has a lovely selection of independent boutiques and shops. They sell an impressive array of items, from handmade jewellery to artisan cheeses, and from vintage clothing to homewares.

These independent stores are run by knowledgeable and friendly owners who have a passion for what they sell. This gives customers a personal shopping experience that is hard to find in larger cities.

Head to Mill Street, Gaol Street or Church Street for some of the best independently owned shops in Oakham.

Oakham’s markets are a long established tradition and popular throughout the town. A regular market takes place every Wednesday and the monthly farmers’ market can be found on the third Saturday of every month.

Rutland County Museum and Oakham Castle both have well stocked gift shops and are the perfect place to look for that something a little bit different.

Notable events taking place each year include the CiCLE Classic road race (April), Rutland CAMRA Beer Festival (June), Rutland County Show (June) and Global Bird Fair (July), Rutland Beer Festival (August), Rutland Food and Drink Week (September) and Christmas late-night shopping (December).

Places to Eat and Drink

One of the most popular dining spots in Oakham is The Wheatsheaf. This historic pub dates back to the 17th century and offers a warm and inviting atmosphere, perfect for a relaxing meal with friends or family. The menu features classic pub fare with a modern twist, and their Sunday roasts are not to be missed. They also offer a wide selection of craft beers and real ales, making it an excellent choice for beer enthusiasts.

Or head to The Grainstore Brewery – especially if you’re a beer enthusiast. This popular brewery offers a wide range of beers, real ales, and ciders, all brewed in-house. Pair your drink with some delicious pub grub to make the most of your visit.

Other town centre restaurants that we’d recommend include Hitchens Barn (but book early as it’s incredibly popular), The Lord Nelson for delicious pizza, The Hornblower for good quality food with a large outdoor summer garden, and The Angler on Mill Street.

Want something a bit more luxurious and don’t mind heading out of Oakham, try Hambleton Hall – a Michelin-starred restaurant where you can indulge in exquisite cuisine and fine wines. The restaurant boasts stunning views of Rutland Water, making it a romantic spot for a special occasion.

Families should head to The Buttercross, on the outskirts of Oakham, with easy parking, for affordable, good quality food. There’s also a small adventure playground here, and plenty of outdoor seating for a summer’s day.

Or if you’re after something more exotic, three good Indian restaurants leave you with good options – Red India, 10 Dining Street, and our favourite – Sarpech.

Where to stay in Oakham?

Work is now complete to transform the hotel formerly known as The Whipper-in, and it’s now known as ‘The George‘ – not to be confused with its namesake in nearby Stamford. This 17th century coaching inn has the best location, right in the heart of Oakham.

The Wisteria Hotel is probably the one we hear the best reviews about. It’s located near the council offices, just a short walk from the shops, restaurants and pubs. They have a beautiful garden to enjoy and the food gets fantastic reviews.

Further down the High Street is the Admiral Hornblower. This popular pub is located in the town centre and offers cosy accommodation and great food/drink in a historic setting. There is also a great beer garden, which is packed in the summer months.

Oakham also has a wide selection of B&B’s and self catering options. Find what you’re looking for on the official Discover Rutland website, or through popular search engines including Booking.com or AirBnB.

Stay just outside Oakham

Head a little further afield and there are two great hotels to choose from at nearby Barnsdale. Rutland Hall Hotel is right on the edge of Rutland Water with great views across the reservoir. Across the road is The Barnsdale which offers a more boutique feel.

For the ultimate luxury break, Hambleton Hall Hotel has 17 individually designed rooms, all of which exude style and sophistication. The hotel also boasts a Michelin-starred restaurant, a wine cellar, and a beautiful garden. Also in Hambleton, you’ll find The Finch’s Arms. It’s one of the most popular restaurants in Rutland and rooms are beautifully furnished.

Oakham is also close to many caravan and campsites. The Rutland Water Campsite is a popular option with excellent facilities and a fantastic location. Other places that crop up regularly are caravan sites at Greetham and Whissendine.

How to get to Oakham

By car: If you’re driving, you’ll find it conveniently located just off the A1 which runs from London to Edinburgh. Oakham is around 100 miles (160 km) north of London and just 22 miles (35 km) from Leicester. If you’re coming from Birmingham, it’s about 60 miles (97 km) east on the M6 and A606, while the journey from Nottingham is roughly 35 miles (56 km) west on the A606.

Once you’re in Oakham, there is plenty of parking available, both on-street and in car parks.

By public transport: There are sadly no longer direct train services from London to Oakham. We hope they return in the future. The two options now are to change for London at either Peterborough or Leicester. You can also drive down to Corby and get a direct train from there.

There are regular bus services to and from nearby cities, towns and villages in the surrounding area.

If you’re coming from outside the UK, the nearest airports are East Midlands, Birmingham, and London Stansted. From here, you can either rent a car or take the train to reach Oakham.

A car journey from Stansted takes 90 minutes, and from Birmingham or East Midlands, the journey takes about an hour.

Final Thoughts

Oakham is a great place to spend a day, or a relaxed weekend away. It’s got easy access to everything around it, some nice places to stay, and a decent choice of places to eat, drink and shop. And with the train station right in the town centre, it’s easy to come and go and spend time in nearby Stamford.