Plan Your Visit to Uppingham: History, Culture, and Countryside

Plan your visit to Uppingham, located in the heart of Rutland, England’s smallest county, and discover a market town full of history, culture, and charm. With its elegant Georgian architecture, and vibrant arts scene, Uppingham offers the perfect mix of traditional English town life.

Whether you’re looking for a relaxing day trip, a cultural weekend getaway, or a base to explore the wider Rutland area, Uppingham has something special to offer.

From its prestigious public school to its lively Friday market, Uppingham seamlessly blends centuries of history with a welcoming, modern atmosphere.

Its ideal location, surrounded by picturesque countryside, quaint villages, and the scenic Rutland Water, makes it perfect for those seeking both relaxation and adventure. What are you waiting for – are you ready to explore all Uppingham has to offer?

Where is Uppingham?

Uppingham is a picturesque market town in Rutland, England’s smallest county. Located just off the A47, a scenic route connecting Leicester to Peterborough, it’s easily accessible from major hubs. The town enjoys excellent road links and is a short drive from railway stations in Oakham and Corby, making it a convenient destination for visitors traveling by car, train, or bus.

So why visit Uppingham and why we’re keen to help you plan your visit to Uppingham? Its cobbled streets, Georgian architecture, and vibrant market square create a charming blend of old-world charm and modern flair. Uppingham School, one of the oldest public schools in England, lends the town a rich sense of history, while its thriving arts scene, including the renowned Goldmark Gallery, ensures there’s always something cultural to enjoy.

Situated in the heart of Rutland, Uppingham is also an excellent base for exploring nearby attractions. A short drive takes you to Rutland Water, one of Europe’s largest man-made lakes, offering activities like cycling, sailing, and birdwatching. Nearby villages such as Lyddington and Wing add to the area’s appeal, with their quaint charm and historical landmarks, making Uppingham an ideal gateway to the best of Rutland.

A Day in Uppingham

A day in Uppingham begins with a leisurely stroll through its historic streets. Plan your visit to Uppingham, and start your morning in the Market Square, the heart of the town, where independent shops and cafes can be found all around. Pop into Scandimania for a coffee and pastry, or browse the wares of local traders at the market. From antiques to artisanal foods, there’s always something to catch your eye.

As you wander, the architectural beauty of Uppingham unfolds. Marvel at the Georgian townhouses and the impressive buildings of Uppingham School, one of England’s oldest public schools. Its chapel and historic classrooms provide a glimpse into a storied past, with notable alumni like Stephen Fry adding to its prestige.

Art lovers will want to stop by the Goldmark Gallery, a hidden gem showcasing contemporary and classic works, ceramics, and rare prints. For lunch, Don Paddy’s offers a cozy retreat with its blend of hearty meals and relaxed ambiance. Afterward, why not walk off your meal on the Uppingham Heritage Trail? This self-guided route weaves through the town’s streets, highlighting landmarks like the Parish Church and hidden courtyards.

As your day winds down, head to The Vaults for a refreshing drink. Located in a 15th-century building, this historic pub is perfect for sampling local ales or enjoying a casual meal.

A Weekend in Uppingham

A weekend in Uppingham offers a chance to enjoy more of its unique blend of history, art, and natural beauty. Begin your getaway by exploring the town’s independent shops and galleries, from the stylish boutiques to antique stores packed with treasures. The Goldmark Gallery is a must-visit for art enthusiasts, while foodie hotspots like Uppingham Fine Foods tempt with local delicacies.

After a day of shopping and strolling, enjoy dinner at The Falcon Hotel, where seasonal dishes and a welcoming atmosphere make for an unforgettable evening. Stay the night in one of the Falcon’s charming rooms, or opt for the elegant Lake Isle Hotel, which combines boutique-style comfort with a refined dining experience.

On your second day, venture a little further afield to discover Rutland’s rural charm. Just a short drive from Uppingham, stunning Rutland Water offers activities for all ages. Rent a bike and cycle its 23-mile perimeter, or take to the water for kayaking or paddleboarding. For a quieter pace, visit Normanton Church, an iconic landmark that offers incredible views over the reservoir.

If you prefer to stay closer to Uppingham, explore the nearby villages of Lyddington and Wing. Lyddington Bede House, with its medieval history and tranquil setting, is a fascinating destination, while Wing Maze provides an intriguing glimpse into ancient traditions.

Wrap up your weekend with a hearty meal at The Crown, where rustic charm and a lively atmosphere guarantee a satisfying end to your Rutland retreat. And hopefully you’re glad you decided to plan your visit to Uppingham.

Things to Do in Uppingham

Uppingham, with its charming streets and rich history, offers something for every visitor. At the heart of the town is its weekly Friday Market, a lively event that dates back to 1281. Held in the historic Market Place, the market is filled with local produce, artisan goods, and unique finds. It’s the perfect place to browse fresh fruit and vegetables, cheese, fish, and flowers, while soaking in the vibrant atmosphere of this traditional market.

For art lovers, Uppingham boasts an impressive selection of galleries and antiques. Visit the Goldmark Gallery and Rutland Gallery to enjoy contemporary and classic art pieces, or head to the Uppingham Antiques Centre to discover rare and antique treasures. If you’re looking for something crafted by local artisans, pop into MADE Gallery in the Market Place or explore the town’s boutique shops offering unique fashion, homeware, and accessories.

History enthusiasts will enjoy a visit to Uppingham School, a prestigious institution founded in 1584. Take a leisurely stroll around the campus to admire the stunning buildings and catch a glimpse of students in their iconic uniforms, further enriching the historic charm of the town.

For those looking to plan your visit to Uppingham and beyond, a visit to Rockingham Castle is a must. Just a short drive from the town, this magnificent castle has been occupied by the same family for over 450 years. The castle offers fascinating historical tours, beautiful gardens, and exciting events throughout the year. Learn about the castle’s rich history, including its role in the English Civil War, and explore the grounds for stunning views over the surrounding countryside.

Nature lovers can also escape into the surrounding Rutland countryside. Explore scenic walking trails and enjoy beautiful views at nearby spots like Eyebrook Reservoir. This peaceful nature reserve is perfect for birdwatching, with opportunities to spot golden plovers, buzzards, and barn owls. The reservoir also holds historical significance, having been used by the RAF for training runs before the famous Dambusters raid during WWII.

After a day of exploration, unwind in one of Uppingham’s welcoming pubs or cafés. The Falcon Hotel is a cozy spot for a traditional afternoon tea, while Don Paddy’s offers cocktails and live music. For hearty, locally sourced fare, The Vaults serves award-winning real ales and delicious pub food in a traditional, welcoming setting. Whether you’re seeking art, history, nature, or relaxation, Uppingham has something special for everyone.

Where to Stay in Uppingham

Uppingham’s accommodation options are as charming and varied as the town itself, offering everything from historic inns to boutique hotels. The Falcon Hotel, a 16th-century coaching inn, is a favorite for its blend of traditional style and modern comforts. Its rooms, each with unique character, offer a cozy retreat after a day of exploring. Guests can also enjoy seasonal menus at its inviting restaurant.

For a more refined stay, the Lake Isle Hotel & Restaurant combines Georgian elegance with contemporary luxury. Its chic rooms, decorated in soft tones and rich textures, make it an ideal choice for couples or special occasions. The hotel’s fine dining restaurant, renowned for its creative use of local ingredients, adds an extra touch of indulgence.

If a laid-back atmosphere is more your style, The Crown Inn provides boutique accommodation in a classic pub setting. With comfortable rooms and a welcoming bar, it’s a great base for exploring Uppingham and beyond.

Eat and Drink in Uppingham

Uppingham’s culinary scene reflects the town’s blend of tradition and sophistication. For an authentic taste of the Mediterranean, No. 23 Restaurant offers vibrant dishes paired with carefully curated wines and cocktails. Its relaxed yet stylish setting makes it a great choice for a celebratory meal.

For a touch of fine dining, head to the Lake Isle Restaurant, where the seasonal menus showcase the best of British cuisine with a modern twist. If you prefer a more casual vibe, The Falcon’s restaurant serves hearty meals in a historic setting, with roaring fires in winter and a lovely garden in summer.

Pub lovers will feel at home at The Crown, known for its traditional menu and live music on weekends. Meanwhile, The Vaults offers a lively atmosphere and a diverse drinks menu, featuring craft beers, cocktails, and local ales.

For a daytime or evening treat, Don Paddy’s combines friendly service with delicious dishes, while Scandimania Coffee House is the perfect spot for a relaxing break with a Nordic-inspired touch.

Plan Your Visit to Uppingham FAQs

Final Thoughts – Plan Your Visit to Uppingham

Uppingham offers a delightful blend of history, culture, and natural beauty that makes it a must-visit destination in Rutland. Whether you’re exploring its charming streets, browsing the weekly market, or enjoying the surrounding countryside, there’s a unique character to the town that captures the essence of rural English life. With its blend of art, tradition, and stunning landscapes, Uppingham provides both a relaxing retreat and an enriching experience for visitors of all ages.

From its historic school and vibrant local arts scene to the peaceful nature reserves nearby, Uppingham proves that sometimes the most memorable experiences come from the quieter, lesser-known gems. Whether you’re planning a short trip or looking for a peaceful getaway it’s important to plan your visit to Uppingham.

The town’s welcoming atmosphere and charming surroundings are sure to leave you with lasting memories.