Things to do in Oakham, Rutland: A local’s guide (2026)
Oakham may be small, but its charm is big – from the lively market square to cozy cafés and a castle with tales to tell. What is it about this tucked-away town that keeps drawing people back?
Located in the heart of England’s smallest county, Oakham is a charming market town full of history, character, and a welcoming community spirit.
In this guide, you’ll discover everything Oakham has to offer – from its historic landmarks like the 12th-century Oakham Castle and quirky horseshoe tradition, to the fascinating exhibits at Rutland County Museum, and the independent shops, cafés, and restaurants along the High Street.
You’ll also find the best places to eat and drink, where to stay for a comfortable night’s rest, practical travel tips, local insider advice, and nearby attractions including the stunning Rutland Water.
Whether you’re planning a day trip, a weekend escape, or a longer stay, this guide will help you explore Oakham and make the most of everything this delightful Rutland town has to offer.
The History and Character of Oakham
With roots stretching back to the Saxon period, Oakham has a rich history that has shaped its unique character over the centuries.
The town developed around its central market, becoming an important hub for trade and agriculture in Rutland. Even today, the charm of its historic streets and traditional architecture gives visitors a real sense of Oakham’s past, from timber-framed buildings to 17th and 18th century townhouses lining the High Street.
The town’s most iconic landmark, Oakham Castle, dates back to the 12th century.
Built by Walkelin de Ferrers, the Lord of the Manor at the time, the castle is less a fortress and more a remarkable example of Norman architecture.
Its Great Hall houses the town’s famous collection of decorative horseshoes, a tradition begun by visiting royalty and nobility, with new additions continuing to this day. This quirky custom is a symbol of Oakham’s enduring heritage and makes the castle a must-see for visitors.
Agriculture has also played a central role in Oakham’s development. From the wool trade in medieval times to the production of grain and other crops, the town has long been a centre for rural industry, linking it to the wider Rutland countryside.
7 Things to Know About Oakham
Before you start exploring, here’s a snapshot of what makes Oakham such a charming and memorable destination.
From its historic streets and landmarks to the friendly local atmosphere, Oakham offers plenty to see, do, and experience – whether you’re visiting for a few hours or staying for a weekend.
1. What to expect
Oakham is a compact, walkable town with a welcoming, relaxed atmosphere.
Visitors can easily explore the main attractions, historic streets, and independent shops on foot, making it ideal for a day trip or a short weekend stay.
While it’s small in size, Oakham has a vibrant community spirit, reflected in local markets, events and cafés that line the High Street.
The town combines history and modern life in a way that feels natural. You’ll find medieval and Georgian architecture alongside contemporary restaurants, craft breweries and boutique shops.
Key landmarks, such as Oakham Castle and the Rutland County Museum, are within easy walking distance, giving visitors a real sense of the town’s heritage without the need for long journeys.
Oakham is also a gateway to the surrounding Rutland countryside. Just a short drive or cycle ride away is Rutland Water, one of the UK’s largest artificial lakes, which offers walking and cycling routes, wildlife spotting and watersports.
2. Things to Do in Oakham
Whether you’re visiting for a day or staying longer, Oakham is compact and walkable, making it easy to explore a variety of attractions, markets, and historic sites without needing a car.
The town’s most iconic landmark is Oakham Castle, a 12th-century Norman building with a stunning Great Hall that houses hundreds of decorative horseshoes.
This centuries-old tradition, started by visiting royalty and nobility, continues to fascinate visitors today. The castle also hosts a Magistrates’ Court once a year, complete with a ceremonial procession that’s a unique spectacle for history enthusiasts and families alike.
Just opposite the council offices, the Rutland County Museum offers an engaging journey through Oakham’s history, covering archaeology, geology, and the town’s agricultural heritage.
The museum’s exhibits include historic farming equipment and artefacts that showcase Rutland’s rural life, and its gift shop is perfect for picking up local souvenirs.
For those who enjoy outdoor spaces, Cutts Close Park provides wide open green areas ideal for picnics, walks, or simply relaxing. The park features a children’s playground, a skatepark, and a pavilion hosting seasonal events, making it a favourite spot for both locals and visitors.
History and architecture enthusiasts will also enjoy All Saints’ Church, a 14th-century landmark with a striking octagonal tower and intricate carvings.
Culture and music are part of Oakham’s charm too. Oakham School, founded in the 16th century, boasts beautiful grounds and regularly hosts student concerts in All Saints’ Church, adding a cultural highlight to any visit.
For those who enjoy craft beers, The Grainstore Brewery is an award-winning local brewery where you can sample a wide range of beers, ciders, and ales, with guided tours available to learn more about the brewing process.
Look out for special events such as the Cider and Sausage Festival that takes place at the Grainstore Brewery in Rutland in Spring.
No visit would be complete without exploring the town’s markets. The Oakham Farmers’ Market (Facebook) takes place on the third Saturday of each month (except December) along Gaol Street and is packed with artisan bread, cheeses, meats, cakes, and fresh vegetables.
Regular markets on Wednesdays and Saturdays also offer plenty of opportunities to discover local produce, crafts, and unique gifts.
For shopping beyond the markets, Oakham has a selection of independent boutiques along Mill Street, Gaol Street, and Church Street, offering handmade jewellery, vintage clothing, artisan food, and homewares.
Annual events such as the CiCLE Classic road race, Rutland CAMRA Beer Festival, Rutland County Show, Global Bird Fair, and Rutland Food & Drink Week mean there’s always something to see or do.
3. Places to Eat and Drink in Oakham
Oakham offers a diverse dining scene, from historic pubs and cosy cafés to Michelin-starred restaurants, ensuring there’s something for every taste and occasion.
One of the town’s most popular spots is The Wheatsheaf, a 17th-century historic pub with a warm, inviting atmosphere. Here, classic pub fare is served with a modern twist, and their Sunday roasts are a must-try. Beer enthusiasts will appreciate the wide selection of craft beers and real ales on offer.
For lovers of locally brewed drinks, The Grainstore Brewery is a must-visit. This award-winning brewery produces a wide range of beers, ales, and ciders on-site, which you can enjoy alongside pub-style dishes in a relaxed setting.
Meanwhile, The Hornblower serves high-quality meals in a friendly atmosphere, with a large outdoor summer garden perfect for warm-weather dining.
Sports fans can head to The Crown Tavern, Oakham’s lively sports bar. It broadcasts all the major football, rugby, and cricket matches on big screens, and the menu offers hearty pub food alongside a great selection of beers and cocktails — ideal for watching the game with friends.
For more formal dining, Hitchen’s Barn delivers modern British cuisine made with locally sourced ingredients, though booking early is highly recommended due to its popularity. Food is also available at The Lord Nelson, while The Angler on Mill Street offers a varied menu for both lunch and dinner.
Those seeking luxury can head just outside Oakham to Hambleton Hall, a Michelin-starred restaurant with exquisite cuisine, fine wines, and stunning views of Rutland Water – perfect for a romantic dinner or special celebration.
Families are well catered for at The Buttercross, which provides affordable meals, outdoor seating, and a small adventure playground for children.
For international flavours, Oakham also has several excellent Indian restaurants. Sarpech is a particular favourite for authentic flavours, while Red India and 10 Dining Street offer more choice.
4. Where to Stay in Oakham
Oakham offers a wide range of accommodation options, from historic inns and boutique hotels to B&Bs, self-catering cottages, and countryside retreats, making it easy to find a place that suits your style and itinerary.
In the heart of town, The George, formerly known as The Whipper-In, is a 17th-century coaching inn with a prime location on the High Street. Its central position allows guests to explore the town’s shops, restaurants, and historic sites entirely on foot, providing a convenient base for a short stay or longer visit.
Close by, The Wisteria Hotel is a highly recommended option, just a short walk from Oakham’s council offices, shops, and dining spots. Guests praise its charming garden and excellent food, making it a popular choice for those seeking comfort and convenience in a town-centre location.
Further down the High Street, The Hornblower combines cosy accommodation with great food and drinks in a historic pub setting. Its spacious beer garden is a summer favourite, offering a lively spot to relax after a day exploring the town.
For visitors who prefer B&Bs or self-catering, Oakham has a variety of options that can be found via the official Discover Rutland website, Booking.com, or Airbnb.
If you’d like to stay just outside Oakham, there are several excellent countryside options. Rutland Hall Hotel sits on the edge of Rutland Water, offering stunning views across the reservoir and stylish, comfortable rooms.
Opposite, The Barnsdale provides a boutique-style experience with individually designed rooms and a peaceful, rural setting.
For a truly luxurious stay, Hambleton Hall Hotel offers 17 individually designed rooms, a Michelin-starred restaurant, wine cellar, and beautifully landscaped gardens.
Nearby, The Finch’s Arms provides elegant rooms alongside one of Rutland’s most popular restaurants.
Oakham and the surrounding areas are also well served for caravan and campsite accommodation.
Rutland Water Campsite is a popular choice with excellent facilities and a fantastic location by the water.
5. Getting to Oakham & Practical Info
Oakham is well connected by road, rail, and air, making it easy to plan a visit whether you’re coming from nearby towns or further afield.
By Car
Oakham is conveniently located just off the A1, which runs from London to Edinburgh. Approximate distances:
- From London: 100 miles (160 km) north
- From Leicester: 22 miles (35 km)
- From Birmingham: 60 miles (97 km) east via the M6 and A606
- From Nottingham: 35 miles (56 km) west via the A606
Once in Oakham, there is plenty of parking available, including on-street spaces and several public car parks around the town centre.
By Train
Currently, there is just one direct commuter-timed train service to and from London to Oakham.
Most visitors travel via Peterborough or Leicester which both have regular connections to Lonon. The other options are to drive to Corby or Market Harborough and travel from there.
By Bus
Regular bus services connect Oakham with nearby cities, towns, and villages in the surrounding area, making it easy to explore Rutland without a car. Check local bus timetables for the latest routes and schedules.
By Air
For international visitors, the nearest airports are:
- East Midlands Airport – ~1 hour drive
- Birmingham Airport – ~1 hour drive
- London Stansted Airport – ~90 minutes drive
From these airports, you can rent a car or use public transport to reach Oakham.
6. Local Tips for Visiting Oakham
To make the most of your visit to Oakham, a few local tips can help you enjoy the town like a seasoned traveller.
The best time to visit is during spring and summer, when the town comes alive with markets, festivals, and outdoor events, and nearby Rutland Water is perfect for walks, cycling, and water activities.
Autumn brings stunning countryside colours, while winter offers a quieter, cozy atmosphere with festive lights and Christmas markets.
Parking in Oakham is generally quite easy, with a mix of on-street spaces and public car parks. However, the town centre can get busy on market days, particularly Wednesdays and Saturdays, as well as during special events.
Arriving early or using one of the larger car parks can save time and stress.
Markets are a highlight of any visit. If possible, plan your trip to coincide with the Oakham Farmers’ Market on the third Saturday of the month, which offers local cheeses, meats, baked goods, and seasonal produce. Even the regular Wednesday markets are worth exploring for fresh local food and artisan crafts.
For a more leisurely experience, try strolling along the Oakham Canal or exploring Cutts Close Park early in the morning for a quiet, scenic start to the day. The independent shops along Mill Street and Church Street are ideal for discovering unique artisan products and handmade items.
When dining, book ahead at popular spots such as Hitchen’s Barn or The Hornblower, especially on weekends or during local events. For pub visits like The Wheatsheaf or The Crown Tavern, arriving early ensures a table, particularly during sports screenings or warm summer evenings.
Planning ahead for seasonal events, including Rutland Food & Drink Week, the Global Bird Fair, or the CiCLE Classic road race, is also recommended as these can affect parking and accommodation availability.
7. Nearby Places to Visit from Oakham
Oakham is not only full of attractions itself, but its location in the heart of Rutland also makes it an excellent base for exploring the surrounding countryside and nearby towns.
Just a short drive from Oakham is Rutland Water, one of the largest lakes in the UK. Popular for walking, cycling, sailing, and birdwatching, it also features nature reserves, picnic spots, and scenic trails. The Rutland Water Nature Reserve is a highlight for spotting rare wildlife and learning about the local ecosystem.
About six miles from Oakham, the market town of Uppingham is known for its historic architecture, independent shops, and the prestigious Uppingham School. With boutique stores, charming cafés, and seasonal events, it’s a lovely destination for a leisurely stroll or a shopping day out.
For history enthusiasts, Rockingham Castle and Burghley House are both within easy reach.
Families and thrill-seekers will enjoy Twinlakes Park in Melton Mowbray, around 20 minutes from Oakham. This award-winning theme park offers rides, attractions, a farm, and outdoor play areas suitable for all ages.
Motorsport fans can make the short trip to Silverstone Circuit, home of the British Grand Prix. The venue also hosts track days, tours, and a museum showcasing the history of Formula 1 racing in the UK.
If you prefer a busier town experience, Market Harborough, around 20 miles (40 minute drive) from Oakham, offers historic streets, independent shops, cafés, and regular farmers’ markets – a perfect mix of shopping and sightseeing.
The charming town of Stamford, about 12 miles (20 minutes by car) away, is renowned for its well-preserved Georgian architecture, boutique shops, and riverside walks.
For a city day trip, Leicester is approximately 22 miles (35–40 minutes by car) from Oakham, with highlights including the King Richard III Visitor Centre, Leicester Cathedral, and a vibrant food and shopping scene.
Oakham FAQs
Here are some of the most frequently asked questions about visiting Oakham, helping you plan your trip with ease.
How do I get to Oakham?
Oakham is accessible by car via the A1 and A606, and is around 100 miles (160 km) north of London. For public transport, trains connect via Peterborough, Leicester, or Corby. Regular bus services link Oakham with nearby towns and villages. The nearest airports are East Midlands, Birmingham, and London Stansted.
What are the must-see attractions in Oakham?
Key attractions include Oakham Castle, Rutland County Museum, All Saints’ Church, Cutts Close Park, and Rutland Water. Don’t miss the monthly Oakham Farmers’ Market for local produce and crafts.
Where is the best place to eat in Oakham?
Popular options include The Wheatsheaf, The Hornblower, The Grainstore Brewery, Hitchen’s Barn, and Michelin-starred Hambleton Hall just outside town. For international cuisine, try Sarpech or Red India.
Are there family-friendly activities in Oakham?
Yes! Cutts Close Park has a playground and open spaces, while Rutland Water offers walking, cycling, and wildlife watching. The Buttercross is a family-friendly pub with outdoor seating and a small adventure playground.
Where should I stay in Oakham?
Stay in the town centre at The George, The Wisteria Hotel, or Admiral Hornblower, or head slightly further afield to Rutland Hall, The Barnsdale, or the luxury Hambleton Hall. There are also B&Bs, self-catering cottages, and caravan/campsites nearby.
When is the best time to visit Oakham?
Spring and summer are ideal for outdoor activities, festivals, and markets. Autumn is perfect for countryside walks, while winter is quieter and charming, with festive events and Christmas markets.
Final Thoughts on Visiting Oakham
Oakham is a hidden gem and one of the main reasons people Love Rutland, offering a unique blend of history, charm, and modern amenities. From the historic Oakham Castle and All Saints’ Church to scenic walks around Rutland Water, there’s plenty to see and do for visitors of all ages.
The town’s compact size makes it easy to explore on foot, whether you’re browsing independent shops, sampling local cuisine at The Hornblower or The Wheatsheaf, or enjoying a coffee at a cosy café. Oakham’s welcoming atmosphere, vibrant markets, and lively events make it feel both relaxing and exciting at the same time.
Whether you’re planning a day trip, a weekend getaway, or a longer stay, Oakham is a destination that rewards curiosity. With convenient transport links, a range of accommodation options, and plenty of local tips to help you make the most of your visit, it’s a town that leaves a lasting impression.
Pack your walking shoes, bring your appetite, and get ready to explore Oakham – a town full of history, local flavour, and the warm hospitality of Rutland.
