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

Located in the heart of Rutland, Uppingham is a picturesque market town full of history, charm, and a friendly, welcoming atmosphere.

In this guide, you’ll discover everything Uppingham has to offer – from its historic streets and independent shops, to the renowned Uppingham School, beautiful architecture, and local cafés and restaurants.

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 Rutland Water and the surrounding Rutland countryside.

Whether you’re planning a day trip, a weekend getaway, or a longer stay, this guide will help you explore Uppingham and make the most of everything this charming Rutland town has to offer.

Uppingham’s History

Uppingham’s history dates back to the Anglo-Saxon period, with its name meaning “higher ground” or “homestead.”

Originally a small settlement, it grew into a thriving market town by the 12th century, attracting traders and settlers due to its strategic location in Rutland.

In the Middle Ages, Uppingham became a key trade hub, known for its busy market and annual fairs. By the 16th century, the town’s importance grew, marked by the construction of many beautiful period homes that still stand today.

The founding of Uppingham School in 1584 was a turning point, establishing the town as a center of education. The school remains one of England’s oldest and most prestigious, continuing to shape the town’s identity.

By 1800, Uppingham was a well-established market town, primarily supported by agriculture. Though the industrial revolution bypassed the area, the town’s rural roots and surrounding farmlands have preserved its agricultural character.

Map of Uppingham

Uppingham is located in the heart of Rutland, England’s smallest county, which is nestled within the East Midlands.

This picturesque town lies approximately 6 miles (10 kilometers) to the southeast of Oakham, the county town of Rutland, and about 20 miles (32 kilometers) from the bustling city of Leicester.

The town sits on the edge of the stunning Rutland Water reservoir, one of the largest artificial lakes in Europe, which adds to the area’s natural beauty and provides a haven for outdoor activities such as walking, cycling, and birdwatching.

Uppingham is easily accessible by road, with the A47 running nearby, connecting the town to larger towns like Peterborough and Leicester.

Things to know about Uppingham

Before you start exploring, here’s a snapshot of what makes Uppingham such a charming and memorable destination.

From its historic streets and striking architecture to the vibrant local community, the town has plenty to offer visitors.

Wander past independent shops and cafés, discover the heritage of the private school, enjoy seasonal markets and local events, or take a stroll in the surrounding Rutland countryside.

1. What to expect

Uppingham is a compact, walkable market town with a relaxed, welcoming atmosphere.

Its historic streets are easy to explore on foot, making it perfect for a day trip or a short weekend stay. Despite its small size, the town has a vibrant community, reflected in local markets, independent shops, cafés, and seasonal events that bring the High Street to life.

The town beautifully blends history and modern life. Key landmarks, such as Uppingham School and St Peter’s Church, are within easy walking distance, allowing visitors to immerse themselves in the town’s heritage without needing to travel far.

Just a short drive or cycle ride away is Rutland Water, offering scenic trails, birdwatching, watersports, and nature reserves.

2. Things to do in Uppingham

Whether you’re visiting for a day or spending a weekend, Uppingham is full of activities that combine history, culture, and the great outdoors.

Compact and walkable, the town allows visitors to explore charming streets, historic landmarks, and local shops with ease.

Explore Rutland Water

Just a short drive from Uppingham, Rutland Water is one of Europe’s largest man-made lakes and a haven for outdoor enthusiasts.

Cycle the 23-mile track around the reservoir, go kayaking or paddleboarding, or enjoy birdwatching along the shoreline.

Don’t miss the striking Normanton Church, partially submerged in the water, which provides breathtaking views – particularly at sunset.

Summer picnics by the lake are a must, and timing your visit to coincide with Uppingham’s Friday Market lets you sample local produce for your outing.

Uppingham Heritage Trail

Discover the town’s rich history by taking the Uppingham Heritage Trail, a self-guided walk through Market Square, the old railway station, the Parish Church, and other historic sites.

Cobblestone streets, Georgian façades, and hidden gems reveal the town’s importance over the centuries and make for a fascinating stroll.

Visit Uppingham School

Founded in 1584, Uppingham School is a prestigious boarding school known for its historic architecture and notable alumni, including Stephen Fry and Rick Stein.

Visitors can admire the impressive buildings and grounds, which form a central part of the town’s heritage.

Arts and Culture at Uppingham Theatre

The charming Uppingham Theatre hosts plays, musicals, and stagecraft classes, making it a hub for local culture.

Whether you want to catch a performance or explore the theatre’s learning opportunities, it’s a great stop for arts enthusiasts.

Nearby Historical Sites

Venture a few minutes outside the town to explore Rutland’s fascinating history:

• Lyddington Bede House (5 minutes away) – A 15th-century almshouse with timber-beamed rooms, carved stone faces, and valley views, originally home to medieval monks.
• Wing Maze (10 minutes away) – An ancient turf labyrinth thought to be a site of pilgrimage and meditation.

Local Events and Markets

Uppingham’s calendar is filled with community events. In June, Feast Day brings live music, street performers, and local stalls to the town centre.

The Fatstock Show in November showcases regional livestock in a traditional auction.

For regular local shopping, the weekly market and independent boutiques provide plenty of opportunities to browse for unique gifts, antiques, and artisan goods.

Explore the Countryside

The rolling Rutland countryside surrounding Uppingham is perfect for scenic drives, walks, and cycle routes. Nearby villages such as Lyddington and Bisbrooke offer charming pubs, farms, and landscapes.

From historic trails and cultural experiences to outdoor adventures and local markets, Uppingham offers something for everyone.

3. Where to Eat and Drink in Uppingham

After a day of exploring, Uppingham offers a variety of dining and drinking options, from traditional pubs to contemporary restaurants, ensuring there’s something to suit every taste.

For a relaxed and authentic pub experience, Don Paddy’s is a must-visit.

This charming spot serves up a variety of tapas dishes, including traditional favourites like patatas bravas and chorizo al vino, alongside an extensive selection of Spanish wines. It’s a great choice if you’re craving an authentic taste of Spain in the heart of Rutland.

For a classic English pub meal, head to The Falcon, overlooking the Market Place. Set in a historic building, it offers locally sourced dishes in a cosy atmosphere, perfect for a hearty meal. In the winter, the roaring log fires create a warm and inviting ambiance, while in warmer months, the outdoor gardens are a delightful spot to enjoy a meal or afternoon tea.

If you’re looking for something more refined, The Lake Isle provides an elegant fine dining experience with contemporary British cuisine made from fresh, locally-sourced ingredients. The restaurant’s seasonal menus, combined with an extensive wine list, offer a memorable dining experience.

For a modern and vibrant atmosphere, No. 23 Restaurant brings a Mediterranean flair to Uppingham, offering everything from carefully curated sharing menus to classic à la carte options.

For a more traditional and hearty pub experience, The Crown is a 16th-century pub that serves a delicious menu of classic pub fare. They also host live music on weekends, creating a lively atmosphere for a pint of local ale or a cocktail.

Lastly, The Vaults, set in a 15th-century building, offers a unique space to relax with craft beers, cocktails, and a menu serving breakfast, lunch, and dinner. The food here includes mouth-watering options like gourmet burgers, making it a perfect place for a relaxed evening pint or casual meal.

4. Where to stay in Uppingham

The Falcon Hotel, located in the heart of Uppingham, is a stunning 16th-century coaching inn that combines traditional charm with modern comforts.

Offering 25 luxurious rooms, each equipped with flat-screen TVs, free Wi-Fi, and tea/coffee-making facilities, it’s an ideal choice for those seeking a relaxing retreat.

The hotel’s inviting atmosphere is perfect for both short breaks and longer stays, and guests can also enjoy delicious meals at the hotel’s restaurant.

For a sophisticated stay, The Lake Isle Hotel & Restaurant provides a perfect blend of Georgian elegance and contemporary luxury. The rooms are designed with calming colours and plush fabrics, creating a serene atmosphere ideal for a romantic getaway or special occasion.

If you prefer a traditional pub experience with the added benefit of boutique-style accommodation, The Crown Inn offers just that. This charming English pub features cozy rooms with all the essentials, including free Wi-Fi, flat-screen TVs, and en suite bathrooms.

5. How to get to Uppingham

By road: Driving is how most people arrive, giving you the flexibility to explore the local area as well. The town is located at the crossroads of the A47 (Leicester to Peterborough) and A6003 (Oakham to Corby) roads. So it’s relatively easy to reach from all directions. 

If you’re travelling from London, you can take the M1 and A14, and you’ll arrive in Uppingham in just under two hours.

By train: The closest railway station is in Oakham, where there are regular train services from Leicester, Peterborough and beyond. From Oakham, you can take a taxi or a bus to reach Uppingham.

If you’re travelling on a budget, catching a bus is a viable option. There are regular bus services from Leicester, Peterborough, and other towns in the surrounding areas.

6. Local Tips for Visiting Uppingham

Make the most of your visit to Uppingham with these insider tips, from getting around the town to enjoying hidden gems and seasonal events.

Best Time to Visit
Spring and summer are ideal for enjoying Uppingham’s outdoor spaces, walking trails, and Rutland Water. Festivals like Feast Day in June bring live music and local stalls, while autumn showcases stunning countryside colours. Winter is quieter but charming, with a cosy atmosphere perfect for exploring historic streets and enjoying local cafés.

Getting Around
Uppingham is compact and walkable, with most attractions, shops, and cafés within easy reach of the town centre. Wear comfortable shoes, especially if you plan to explore cobbled streets or take the Heritage Trail.

Parking Tips
Street parking and small public car parks are available, but spaces can fill quickly during market days or festivals. Arrive early for the best spots or use a car park slightly outside the town centre for a short walk into town.

Markets and Local Produce
The Friday Market is a highlight, offering fresh local produce, artisan bread, and seasonal treats. Plan your visit around market day for the best experience. Regular shopping in independent boutiques along High Street and nearby streets is also worth a leisurely stroll.

Dining & Reservations
Popular restaurants and pubs can get busy during weekends or festivals. Book ahead where possible, and arrive early at pubs for lunch or dinner, especially during summer evenings.

Seasonal Events
Keep an eye on Uppingham’s calendar:

• Feast Day (June) – music, street performers, and local stalls.
• Fatstock Show (November) – traditional livestock auctions showcasing cattle, sheep, and pigs.

With a little planning, these local tips will help you explore Uppingham like a pro, discover hidden corners, and enjoy all the town has to offer.

7. Things to do nearby

Uppingham’s central location makes it the perfect base for exploring some of Rutland and its surrounding areas’ top attractions, with plenty to see and do just a short drive away.

One must-see destination is Burghley House, located just a 25-minute drive from Uppingham in the historic town of Stamford.

This stunning Elizabethan mansion is set in over 200 acres of parkland and is renowned for its grand state rooms, exquisite gardens, and impressive art collections.

The house itself is an architectural marvel, while the grounds offer peaceful walks and beautiful vistas, making it an ideal spot for a leisurely day out. Burghley House is also home to the annual Burghley Horse Trials, a prestigious event that attracts equestrian enthusiasts from around the world.

For a more relaxed experience, head to Barnsdale Gardens, just 15 minutes from Uppingham. Created by the famous British gardener Geoff Hamilton, this inspiring collection of 38 individual gardens showcases a variety of styles and themes.

Whether you’re an avid gardener or simply appreciate the beauty of nature, Barnsdale’s well-kept gardens offer something for everyone. In the autumn months, the display of seasonal colors is truly breathtaking, with vibrant reds, oranges, and golds transforming the landscape into a painter’s palette.

For a unique and educational experience, take a trip to Rutland Water (just a short drive away), where you can enjoy not only the scenic reservoir but also a host of other attractions.

The Rocks By Rail Museum in nearby Cottesmore is a hidden gem for railway enthusiasts, offering a fascinating collection of vintage trains and railway memorabilia. Alternatively, explore Rutland Water Nature Reserve, which is home to a wealth of birdlife, including ospreys during the breeding season, making it a popular spot for birdwatching.

If you’re interested in history, Rockingham Castle (about 20 minutes away) is a must-see. This 11th-century castle, built by William the Conqueror, offers a fascinating glimpse into medieval life, along with stunning views of the surrounding countryside. It’s also the perfect place for a leisurely walk through the beautiful grounds or a traditional afternoon tea in the castle’s tearoom.

For those who enjoy exploring historic towns, Oakham (about 11 miles from Uppingham) is a lovely town with a rich history and charming atmosphere.

Visit Oakham Castle, a well-preserved Norman castle with an impressive collection of over 200 horseshoes, gifted by visiting nobility. The town also hosts a vibrant market and several independent shops, offering a perfect opportunity for a relaxing afternoon out.

Final Thoughts on Visiting Uppingham

Whether you’re exploring the Uppingham Heritage Trail, admiring the prestigious buildings of Uppingham School, or enjoying outdoor activities at Rutland Water, there’s plenty to keep you entertained.

The town’s vibrant local events, from Feast Day to the Fatstock Show, provide an authentic taste of Rutland life, while its independent shops and cafés make for a relaxed, leisurely visit.

Uppingham’s compact size makes it easy to explore on foot, but its location also allows for day trips to nearby highlights such as Oakham, Stamford, Market Harborough, and the surrounding Rutland countryside.

With charming accommodation options, great dining experiences, and a range of cultural and outdoor activities, Uppingham is ideal for a day trip, weekend escape, or longer stay.