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If you are tired of the usual dinner and drinks routine, long distance walks in England offer a refreshing alternative. Walking side by side removes the pressure of staring across a table, gives you endless things to talk about, and lets you see how someone copes with blisters, hills and changeable weather. Plenty of couples say they got to know each other better in a week on the trail than in months of dates, and the fresh air does wonders for the mood too.
You do not need to be an athlete or tackle a whole route in one go. Many people dip into a stretch for an afternoon or a weekend. This guide introduces some of the best known trails, then covers preparation, kit, safety and how to make a walk feel like a proper date rather than a route march.
Why Long Distance Walks in England Make Great Dates
Walking is one of the most underrated ways to connect. There is no need to fill silences, because the scenery does the work. Conversation arrives naturally, drifts away, and returns again. Because you are side by side rather than face to face, many people find it easier to open up.
A walk also tells you plenty about a person. Are they patient when the path is muddy? Do they share their snacks? Can they laugh when it starts to rain? These small moments are more revealing than any carefully rehearsed dinner conversation. Walking together is free or cheap, healthy, and adaptable to any fitness level.
Of course, it is wise to start small. For a first date, a long trek is a big commitment, so choose a short section of a trail, with a pub or a cafe at the end. Save the multi day plans for when you know each other well.
South West Coast Path
The longest of England’s waymarked routes, the South West Coast Path runs for around 630 miles from Minehead in Somerset, around Devon and Cornwall, to Poole Harbour in Dorset. Distances are commonly quoted this way, but check the official trail website for the latest figures.
Nobody walks it all in one go on a date, but its great strength is how easy it is to pick off a small piece. You can choose a gentle clifftop stroll between two villages, catch a bus or train back, and finish with fish and chips by the harbour. Expect dramatic coastline, hidden coves and plenty of ups and downs, so it can be tiring. The scenery is spectacular, which is exactly what you want when you are trying to impress someone.
Cotswold Way
Running for roughly 100 miles from Chipping Campden to Bath, the Cotswold Way is a National Trail and is a gentle, pretty route through honey coloured villages, rolling hills and beech woods. It is well signed and has lots of cosy pubs and tea rooms along the way, which suits couples who like their walking with a side of comfort.
It is also a good first multi day challenge. Many walkers split it over five to eight days, with baggage transfer services and accommodation easy to arrange in advance. Short sections, such as Broadway to Winchcombe, make great day dates. Look out for the Cotswold escarpment views and historic landmarks, and leave time to stop and enjoy them.
Hadrian’s Wall Path
If you like your walks with history, Hadrian’s Wall Path follows the line of the Roman frontier for around 84 miles from Wallsend, near Newcastle, to Bowness on Solway in Cumbria. You pass forts, turrets and milecastles, and the landscape of Northumberland is wild and beautiful.
The central section around Housesteads Fort is the most dramatic, with ridges and crags, but it is also more demanding than the gentler eastern and western ends. Keep in mind that weather can change quickly on exposed sections, so be ready for wind and rain. It is a great choice for couples who love history, photography or a sense of adventure, and one of the most memorable long distance walks in England for anyone who enjoys a story with their scenery.
South Downs Way
The South Downs Way is about 100 miles long, stretching from Winchester in Hampshire to Eastbourne in East Sussex. It follows chalk ridges and open grassland, with huge skies and sea glimpses, much of it fairly easy underfoot compared with mountainous routes.
Because it is close to London and the south coast, it is easy to reach by train and ideal for day dates. Highlights include the Seven Sisters cliffs near the finish, Devil’s Dyke and the quiet villages with welcoming pubs. Since some stretches are exposed, take water, sun protection and a layer in case of wind.
Pennine Way
Often called the backbone of England, the Pennine Way is a tougher proposition at around 268 miles, running from Edale in the Peak District to Kirk Yetholm in the Scottish Borders. It crosses high moorland, remote country and boggy ground, and it needs good navigation skills and sturdy kit.
This is one for experienced walkers, or for couples who already know they love a challenge. If you want a taste without the full commitment, try the opening section from Edale, a lovely day out with the great views over Kinder Scout and plenty of public transport options. Do not underestimate it, because the weather on high ground can turn fast.
Peddars Way and Norfolk Coast Path
Not every great route is mountainous. The Peddars Way in Norfolk runs for around 46 miles along an ancient Roman road, from Knettishall Heath towards the coast at Holme next the Sea, where it links with the Norfolk Coast Path. It is gentle, relatively flat and perfect for couples who prefer a leisurely stride and big skies to steep climbs.
This is a good National Trail for beginners, with quiet lanes, farmland, woodland and eventually the salt marshes and beaches of the north Norfolk coast. Combine it with the coast path and you have a lovely week long journey with seafood and seaside pubs to look forward to.
How to Choose the Right Route
When choosing among long distance walks in England, the best route is the one that suits both of you, not the one that looks hardest on a map. Be honest about fitness, time and experience. Ask yourselves a few questions:
- How far can we each comfortably walk in a day? Start with 5 to 8 miles if you are unsure.
- Do we want a challenge or a relaxed stroll?
- How easy is it to get to the start and home from the finish by train or bus?
- Is there somewhere to eat, drink and stay nearby?
- What time of year suits us? Summer is popular, spring and autumn are quieter, and winter days are short.
The official National Trails website has maps, route descriptions and itinerary ideas for each route, so use it for up to date information on closures, diversions and facilities. Local walking groups can also be a friendly way to try out the style before committing to a bigger trip.
Preparation and Training
You do not need a special fitness programme, but a bit of preparation makes everything more fun. Build up with a few shorter walks in the weeks before. Try different surfaces and some hills, so your legs and feet get used to it. Break in new boots well before the big day, as nothing ruins a date like blisters.
Plan your route in detail, because even the most gentle of the long distance walks in England can catch out walkers who set off without a clear idea of the miles. Work out where you will start and finish each day, where to eat and refill water, and where you might bail out if someone gets tired. Book accommodation early for popular routes in summer. Check the weather forecast a few days before and again on the morning, and be ready to switch plans if it looks nasty.
Kit and What to Pack
Good kit makes a huge difference. You do not need the most expensive gear, but a few essentials are worth getting right:
- Comfortable, broken in walking boots or shoes with good grip
- Waterproof jacket and layers, because British weather can change in minutes
- Small rucksack with water, snacks and a first aid kit including blister plasters
- Map, compass or a fully charged phone with a downloaded offline map and a spare battery pack
- Sun cream, hat and sunglasses in summer, gloves and hat in cold weather
- Whistle and head torch for longer days
- Cash or card for cafes and pubs, as signal and payments can be patchy in rural places
Share the load fairly and agree who carries what. Pack lightly, and treat each other to a small surprise, such as a flask of hot chocolate or a favourite snack.
Safety on the Trail
Most walks are perfectly safe if you take sensible precautions. Tell a friend or family member where you are going and when you expect to return. Stay on marked paths, follow the Countryside Code and close gates behind you. Keep a close eye on the weather, and turn back if conditions get worse.
If you are walking with someone new, it is wise to meet in a public place first and choose a well used, popular stretch of trail for your initial walk. Share your live location with a trusted friend, and trust your instincts. Our guide to red flags on a first date will help you stay alert. In an emergency, call 999 and ask for the police, or for mountain rescue if you are in the hills.
Talking on the Trail
Walking is brilliant for conversation, but it helps to have a few ideas ready. You could ask about their favourite trip, what they would do with a free year, or the best meal they ever ate. Our list of questions to ask before a first date works just as well on a footpath.
Do not feel you must talk constantly. Companionable silence is a good sign, and it gives you time to enjoy the view. Offer snacks, point out interesting things, and notice how your companion reacts to challenges. Keep your phone for photos and maps rather than scrolling. If you are planning something more adventurous later, our article on third date ideas has plenty more inspiration.
Frequently Asked Questions
Are long distance walks suitable for a first date? A short section is. A multi day trek is too big a commitment for a first meeting, so keep to a few miles with a pub or cafe at the end.
What is the easiest long distance trail in England? Routes such as the Peddars Way, the gentler parts of the South Downs Way and sections of the Cotswold Way are good for beginners. Always check current route conditions first.
Do I need to book accommodation? For multi day walks, yes, especially in summer. Book well ahead for popular routes, and look at baggage transfer services if you want to walk with a light pack.
What if one of us is slower? Walk at the slower person’s pace and plan shorter days. It is not a race, and patience is attractive.
Is it safe to walk alone or with someone new? Choose popular paths, tell someone your plans, share your location and trust your instincts.
The Bottom Line
England has a wonderful network of trails, and long distance walks in England do not have to be an extreme sport. You do not need to be an experienced hiker to enjoy them as a couple. Start with a gentle section, wear comfortable boots, pack sensibly and let the scenery and the conversation do the rest. If it goes well, you might even find yourselves planning the next stretch together.
For more date inspiration and dating advice, visit Singles Warehouse, or get in touch if you would like to ask us anything.
