Kirkby Stephen Tours in May 2026
Planning for a trip to Kirkby Stephen during May? We offer 10+ tour packages to Kirkby Stephen departing in May 2026 that have 20+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Kirkby Stephen on your May holiday.
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10 Best May 2026 Tours in Kirkby Stephen
Join one of these handpicked Kirkby Stephen May 2026 tour packages, tailored to the season.
Take your time to savor England’s most iconic footpath with the 'Coast to Coast Guided Explorer – 17 Days' tour. This extended guided walking trip stretches from St Bees on the Irish Sea to Robin Hood’s Bay on the North Sea, offering two extra days compared to the classic itinerary for a more in-depth experience.
Traverse the famed Lake District, Yorkshire Dales, and North York Moors national parks, clocking in at approximately 315km (195 miles) of moderate to challenging hiking. The extra days allow for a gentler pace and more opportunities to explore quaint villages, rolling hills, and the mystical Nine Standards Rig. Enjoy the camaraderie of a small group, led by a knowledgeable guide, and relax each night in welcoming hotels, guesthouses, and traditional pubs.
Along the way, you’ll marvel at the diversity of the English countryside, from rugged mountains and serene lakes to dry stone walls and vibrant market towns. Celebrate your achievement on the shores of the North Sea with your fellow walkers—a moment you’ll cherish.
The unique selling point of this trip is its leisurely, immersive approach—perfect for travelers who want to fully absorb the landscapes, history, and local character of England’s legendary Coast to Coast walk.
17 days
Embark on the second section of Wainwright’s Coast to Coast with this 11-day walking tour from Kirkby Stephen to Robin Hood’s Bay—ideal for experienced travelers and seniors looking for moderate activity. This thoughtfully paced itinerary breaks up tougher sections, granting you extra time to savor the Yorkshire Dales, North York Moors, and charming market towns like Richmond. Traverse river valleys, climb the mystical Nine Standards Rigg, and make your celebratory entrance into Robin Hood’s Bay on the North Sea. The tour features cozy accommodations and highlights the diversity of England’s countryside and hospitality. The unique aspect is its relaxed pacing, allowing for deeper exploration and greater enjoyment of each destination.
11 days
Cover the first half of the Coast to Coast Walk from St Bees to the village of Kirkby Stephen crossing the Lake District National Park. Experience the most dramatic section of Wainwright’s legendary Coast to Coast route on this self-guided walking holiday from the Irish Sea at St Bees to the market town of Kirkby Stephen. The western half of the Coast to Coast offers some of the most spectacular scenery in northern England, crossing the rugged heart of the Lake District National Park and into the edge of the Yorkshire Dales.
This 9-day itinerary cleverly splits the final long stage between Shap and Kirkby Stephen into two shorter days, giving you a more relaxed finish without losing any of the route’s highlights. It’s ideal if you’re short on time, new to long-distance walking, or want to enjoy the trail at an easier pace while still experiencing the best-loved landscapes of the Coast to Coast.
Your journey begins by dipping your boots in the Irish Sea at St Bees, then heading east with the prevailing wind at your back. You’ll walk through dramatic valleys such as Ennerdale, Borrowdale, and Patterdale, pass shimmering lakes, and cross high passes with the option to tackle famous summits like Helvellyn. As the Lake District fells give way to the gentler landscapes of the Yorkshire Dales, you’ll finish in Kirkby Stephen, a charming market town on the edge of the Yorkshire Dales with rail links—perfect for a celebratory rest after an inspiring week on the trail.
Prefer a faster pace? Our 8-day version (trip code UCT) keeps the classic long stage between Shap and Kirkby Stephen intact for a more challenging itinerary.
Scroll down to explore all our Coast to Coast walking options.
9 days
Explore the iconic Coast to Coast Walk at your own pace with this 9-day trip from Kirkby Stephen to Robin Hood’s Bay. Perfect for seasoned explorers and seniors, this moderate walking tour covers the Yorkshire Dales and North York Moors, with long days and rewarding views. Begin with a hike over the Pennines and follow the River Swale to Richmond before journeying through the moors to the dramatic North Sea coast. Stay in welcoming local inns and guesthouses, and enjoy the camaraderie of fellow walkers. The tour’s highlight is the chance to complete the celebrated second half of the Coast to Coast walk, culminating in a triumphant arrival at Robin Hood’s Bay.
9 days
Begin your British hiking adventure on the Coast to Coast: St Bees to Kirkby Stephen tour, an 8-day moderate walking journey crafted for experienced and senior travelers. Start at the Cumbrian seaside resort of St Bees and traverse the Lake District’s dramatic scenery, passing through valleys, national parks, and picturesque villages. Encounter working hill farms, traditional pubs, and the charm of English market towns. This self-guided trip includes comfortable accommodations and convenient transport. The unique selling point lies in experiencing the first half of the iconic Coast to Coast trail, blending mountain landscapes with classic English hospitality and heritage.
8 days
Walk the famous Coast to Coast trail guided from St Bees to Robin Hood's Bay. For those seeking a more relaxed pace on one of Britain’s most iconic long-distance trails, our 17-day guided Coast to Coast Rambler walk is the perfect option. While the classic Wainwright route is typically completed in 15 days, this extended itinerary allows extra time to appreciate the journey, engage with the landscape, and enjoy the camaraderie of a small, guided group. Covering approximately 315km (195 miles) across three spectacular national parks, this is English hillwalking at its finest — made all the more rewarding with thoughtful pacing and expert support. Though slightly gentler, the hike remains a true challenge and a deeply satisfying achievement. The adventure begins in the seaside village of St Bees on the Irish Sea, climbing into the dramatic Lake District, where mountain passes and serene lakes appear early in the walk. From there, the trail winds through the Yorkshire Dales, over the mystical Nine Standards Rigg, and along the River Swale to the historic town of Richmond. The 17-day version gives more time to explore the North York Moors, breaking up longer days between Richmond and Blakey before reaching the North Sea coast. The journey ends at Robin Hood’s Bay, where tradition calls for dipping your boots in the sea — and celebrating with a pint, ice cream, or glass of fizz. Along the way, stay in handpicked guesthouses, country inns, and cosy hotels, all known for their warm welcomes and hearty meals. Each day brings timeless villages, dry stone walls, and satisfying English breakfasts. It’s remarkable that this trail was only designated a National Trail in 2022, nearly 50 years after Wainwright’s vision. Walk it with us and discover why it remains a national treasure. Scroll down to compare all our Coast to Coast options and find the journey that suits your walking style best.
17 days
Cover the first half of the Coast to Coast Walk from St Bees to the village of Kirkby Stephen crossing the Lake District National Park. Experience the most dramatic section of Wainwright’s legendary Coast to Coast route on this self-guided walking holiday from the Irish Sea at St Bees to the market town of Kirkby Stephen. The western half of the Coast to Coast offers some of the most spectacular scenery in northern England, crossing the rugged heart of the Lake District National Park and into the edge of the Yorkshire Dales.
This 9-day itinerary cleverly splits the final long stage between Shap and Kirkby Stephen into two shorter days, giving you a more relaxed finish without losing any of the route’s highlights. It’s ideal if you’re short on time, new to long-distance walking, or want to enjoy the trail at an easier pace while still experiencing the best-loved landscapes of the Coast to Coast.
Your journey begins by dipping your boots in the Irish Sea at St Bees, then heading east with the prevailing wind at your back. You’ll walk through dramatic valleys such as Ennerdale, Borrowdale, and Patterdale, pass shimmering lakes, and cross high passes with the option to tackle famous summits like Helvellyn. As the Lake District fells give way to the gentler landscapes of the Yorkshire Dales, you’ll finish in Kirkby Stephen, a charming market town on the edge of the Yorkshire Dales with rail links—perfect for a celebratory rest after an inspiring week on the trail.
Prefer a faster pace? Our 8-day version (trip code UCT) keeps the classic long stage between Shap and Kirkby Stephen intact for a more challenging itinerary.
Scroll down to explore all our Coast to Coast walking options.
9 days
Walk the second section of the Coast to Coast through the Yorkshire Dales and North York Moors at a more comfortable pace. This rewarding eastern section of Alfred Wainwright’s legendary Coast to Coast walk takes you from the rugged Pennines, through the Yorkshire Dales, and across the beautiful North York Moors National Park to the dramatic cliffs of the North Sea. This extended 11-day itinerary breaks up the middle stages of the route, allowing for shorter daily distances, more time to explore the scenery, and a more relaxed pace through one of England’s most charming walking regions.
Your journey begins in the Pennines Area of Outstanding Natural Beauty, climbing the mystical Nine Standards Rigg before descending into the rolling green hills and timeless villages of the Yorkshire Dales. Follow the meandering River Swale into the historic market town of Richmond, then continue towards Blakey and the heather-covered slopes of the North York Moors. From here, the trail rolls dramatically towards the coast, ending with a triumphant arrival in Robin Hood’s Bay. Tradition calls for dipping your boots in the sea and celebrating with a pint, a glass of champagne, or an ice cream on the beach!
Along the way, you’ll experience classic English landscapes of dry stone walls, historic market towns, and friendly village pubs. Accommodation is in cosy small hotels, traditional inns, and welcoming guesthouses—places that showcase the warmth and hospitality of rural England.
If you’d like a faster-paced adventure, our 9-day version of this itinerary (trip code WCO) keeps the final two days between Richmond and Blakey Ridge intact for a more traditional challenge. Scroll down to explore all of our Coast to Coast walking options.
11 days
Follow the Coast to Coast Walk from St Bees towards the historic villages and beautiful landscapes of the Yorkshire Dales. Experience the most dramatic section of Wainwright’s legendary Coast to Coast route on this self-guided walking holiday from the Irish Sea at St Bees to the market town of Kirkby Stephen. The western half of the trail showcases some of the most spectacular scenery in northern England, taking you across the rugged heart of the Lake District National Park and into the edge of the Yorkshire Dales.
If you're short on time, new to long-distance walking, or prefer to explore the route in manageable stages, this itinerary is an ideal way to sample the best-loved landscapes of the Coast to Coast. It’s also perfect for hikers who simply want the thrill of crossing the Lake District on foot, experiencing the quiet valleys, shimmering lakes, towering peaks and traditional fellside villages. You’ll start your journey by dipping your boots in the Irish Sea at St Bees, then head east with the prevailing wind at your back. The route leads through dramatic valleys such as Ennerdale, Borrowdale, and Patterdale, with the chance to take optional high-level detours to iconic Lakeland summits like Helvellyn. As the Lake District fells give way to the gentler landscapes of the Yorkshire Dales, your walk concludes in Kirkby Stephen, a charming town with rail links and a great place to relax after an inspiring week on the trail.
Looking to take things at a gentler pace? Our 9-day version of this trip (trip code WSK) breaks up the longer stage between Shap and Kirkby Stephen, offering a more relaxed alternative.
Scroll down to explore all our Coast to Coast walking options.
8 days
The world famous Coast-to-Coast is an exhilarating long-distance walking route originally described by the writer Alfred Wainwright in his book of the same name. First published in 1973, the book has grown in renown and today is as popular as ever, with the walk itself featuring on the bucket list of all keen walkers.
At nearly 200 miles in length, the route takes you across country, up fells and down dales, from Cumbria's St Bees, on the shores of the Irish Sea, to the picturesque fishing village of Robin Hood's Bay in Yorkshire, passing fabulous landscapes at every turn.
The tour runs through three national parks in northern England - the Lake District, the Yorkshire Dales and the North York Moors - and features some of the most spectacular and beautiful scenery in the country.
The walking is challenging and recommended for experienced fell walkers and confident map readers only, but the sense of achievement and camaraderie when you encounter fellow coast to coasters makes it all worthwhile.
Your accommodation each night is in carefully picked B&Bs, with either ensuite or private facilities, where friendly smiles and warm welcomes to weary walkers are guaranteed!
Please note that GPX tracks and a routes and maps guide are provided on this trip, along with our usual maps. This replaces our usual turn by turn route directions.
18 days
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