Things to do in Uppingham, Rutland: A Local’s Guide

Visiting Uppingham, in the charming county of Rutland, feels like stepping back in time. This small and perfectly formed English town boasts cobbled streets, Georgian architecture, and historic charm, paired with vibrant arts, cozy cafes, and picturesque countryside.

Famous for its prestigious public school and thriving arts scene, Uppingham is an ideal destination for those seeking history, culture, and scenic walks in the heart of England’s smallest county.

A leisurely stroll through Uppingham reveals beautifully preserved Georgian buildings that line the historic High Street. They reflect the town’s unique blend of heritage and creativity and every corner reveals independent shops, antique stores, and inviting places to eat and drink. Be sure to visit Don Paddy’s for a hearty brunch or indulge in Nordic-inspired treats at Scandimania, a cozy coffee shop beloved by locals.

Art enthusiasts will no doubt be drawn to the renowned Goldmark Gallery, a family-run institution that has hosted art exhibitions, ceramics, and rare prints for over 40 years. Its continued reputation as a cultural hub has made it a must-visit destination for anyone exploring the area.

And no visit to Uppingham would be complete without delving into its educational legacy. At the heart of the town lies Uppingham School, one of the oldest public schools in England, founded in 1584. Its historic chapel and school buildings – where notable alumni such as Sir Malcolm Sargent and Stephen Fry once roamed – can be seen throughout the town centre. 

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.

Today, Uppingham is a charming blend of historic homes, a world-renowned school, and a thriving community that honours its past while embracing the future.

Map of Uppingham

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

Despite its rural setting, Uppingham is well-connected to major transport links, making it a convenient base for exploring the surrounding areas. Whether you’re looking to discover more of Rutland’s charming villages or venture into nearby cities, Uppingham is perfectly positioned to offer the best of both worlds.

Things to do in Uppingham

Uppingham offers a delightful mix of outdoor activities, historical exploration, and cultural experiences, making it a perfect destination for a day trip or a longer stay.

For outdoor enthusiasts, Uppingham is ideally located to explore the stunning countryside of Rutland. Just a short drive away is Rutland Water, one of Europe’s largest man-made lakes. This scenic spot is perfect for a range of activities: rent a bike and cycle the 23-mile track around the reservoir, spot rare birds, or take to the water for kayaking, sailing, or paddleboarding. Don’t miss Normanton Church, a striking, partially submerged landmark that offers breathtaking views across the water, especially at sunset. During the summer, picnics by the shore are a must—time your visit to coincide with Uppingham’s Friday Market for some delicious local produce.

If you’re keen to explore more of the area’s rich history, a visit to the Rutland County Museum in nearby Oakham is a great way to delve into the past. Housed in a historic building, the museum showcases the history of Uppingham and Rutland, from Iron Age relics to Victorian life.

Beyond Uppingham, the surrounding villages offer even more to discover. In Lyddington (just a 5-minute drive away), visit the Bede House, a 15th-century building once home to medieval monks and later transformed into an almshouse by the Bishop of Lincoln. Its timber-beamed rooms, carved stone faces, and expansive valley views offer a fascinating glimpse into medieval life. A little further on, in Wing (10 minutes away), you’ll find the Wing Maze, an ancient turf labyrinth thought to have been a place of pilgrimage and meditation.

Back in Uppingham, one of the best ways to learn about the town’s history is to follow the Uppingham Heritage Trail, a self-guided walk that takes you through some of the town’s most historic sites, including the Market Square, the old railway station, and the Parish Church. As you stroll along cobbled streets and past beautiful Georgian buildings, you’ll uncover hidden gems and discover Uppingham’s significance over the centuries.

For a deeper dive into Uppingham’s academic history, visit Uppingham School, a prestigious boarding school founded in 1584. The school’s impressive architecture and historic buildings are not only a vital part of the town but also home to famous alumni such as Stephen Fry and Rick Stein.

If you’re a fan of the arts, be sure to check out the Uppingham Theatre, a charming venue offering a variety of performances, from plays to musicals. The theatre also hosts acting and stagecraft classes, so it’s worth a visit if you’re interested in learning more about theatre.

Uppingham’s calendar is filled with local events throughout the year. In June, Feast Day sees the town come alive with local stalls, live music, and street performers. Another unique event is the Fatstock Show in November, which brings together farmers from the surrounding countryside to showcase their cattle, sheep, and pigs in a traditional livestock auction.

For those who enjoy shopping, Uppingham has a wide range of independent stores, boutiques, and a weekly market. Whether you’re looking for unique gifts, antiques, or simply want to browse, Uppingham offers a delightful shopping experience.

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 Rutland Railway 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 quaint villages, Oakham (about 13 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.

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. Set in a 300-year-old building, it’s a neighbourhood restaurant with a carefully selected wine list, refined cocktails, and a great selection of beers. The Sunday roast is particularly popular.

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.

With so many options, Uppingham is a great place to enjoy a memorable meal, whether you’re after traditional pub fare, Mediterranean cuisine, or fine dining in a historic setting.

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 those who want to explore the rooms before booking, The Falcon offers full 360-degree virtual tours of each room on its website, ensuring you find exactly what you’re looking for.

For a more 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. In addition to its comfortable accommodation, The Lake Isle is also home to a fine dining restaurant, where you can indulge in seasonal dishes paired with an extensive wine list, making it a fantastic choice for those looking to combine relaxation with gourmet experiences.

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. The Crown’s relaxed and welcoming atmosphere makes it a great option for those looking for a comfortable and affordable stay while being close to Uppingham’s attractions. With the added bonus of a traditional pub downstairs, guests can enjoy a meal or a pint after a day of exploring.

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.

Plan your visit with Love Rutland

From wandering the cobbled streets, enjoying locally sourced food and drink, to venturing out into the surrounding countryside and waters, Uppingham is a really great place to visit. Its beautiful old buildings, friendly community, and lively market give it a unique character that’s hard to find elsewhere. The iconic Uppingham School, along with the town’s thriving arts scene, adds a distinctive flair to this picturesque market town. Whether you’re visiting for a leisurely weekend or a longer stay, the town’s history, culture, and natural beauty ensure that there’s always something to discover.

For more inspiration and all the tips you need to help you plan your visit, check out the rest of our Uppingham guides. We’ve gathered everything you need to organise your trip, from accommodation and dining recommendations to local events and activities.