Waypoint Escape: Winchester Countryside 18.5km Hike + Pub Drinks

Waypoint is London’s close-knit, adventure-loving crew for like-minded legends in their 20s–40s. Think big hikes, belly laughs, incredible scenery, and well-earned pints with great people.

Can you believe it’s been 2 years since we launched Waypoint Crew? Where has the time gone?! What an amazing community we’ve built together 💛

To keep the birthday celebrations going, we’re heading back to Winchester (Beth’s hometown!) for a stunning 18.5km countryside hike through rolling hills, riverside paths, and classic Hampshire villages.

We’ll start from Winchester train station, heading past Winchester Cathedral for a quick look, before making our way out towards Easton and on to Avington. We’ll stop for a picnic lunch in the beautiful Avington Park, before continuing to Itchen Abbas in the South Downs National Park.

From there, we’ll make a quick stop at The Plough (Beth’s local) for refreshments and a toilet break, then follow the River Itchen back through Chilland into Winchester.

We’ll finish with a space reserved at one of our absolute favourites - The King Alfred Pub in Winchester Town 🍺🎈, where you can join for post-hike celebrations, or head straight back to the station for trains to London (10-minute walk away from the pub).

• Date: Saturday 25th April 2026
• Meet: 9:30am (train arrives 9:26am)
• Hike Start: 9:50am
• Picnic Lunch Stop: ~12:00pm (30 mins)
• Refreshment & Toilet Stop: ~1:00pm – The Plough, Itchen Abbas
• Finish: ~4:30pm, Winchester Town
• Optional Pub Stop: The King Alfred, 11 Saxon Road, SO23 7DJ - 10-minute walk from the train station
• Distance: 18.5km / 11.4 miles
• Time on Trail: ~4.5 hours
• Grade: Moderate (some steep hills)
• Route: Circular

Beth – Founder of Waypoint Crew and qualified Lowland Leader. Beth loves countryside adventures that finish with a cold pint and built Waypoint Crew as a space for people who love adventure and a laugh.

Jon – A total legend and regular at Waypoint events. Recently qualified as a Lowland Leader with Mountain Training, Jon helps lead hikes and makes sure everyone has an amazing day outdoors.

9:30am | Meet
Outside Winchester Train Station. Trains run regularly from London, including one arriving at 9:26am. Come say hi and meet your crew.

9:50am | Hike Begins
Quick briefing and we’re off. Please arrive on time - if delayed, message in the WhatsApp group.

~12:00pm | Picnic Lunch
Lunch stop overlooking the beautiful Avington Park.

~1:00pm | Refreshment Stop
The Plough, Itchen Abbas (toilets + quick refreshments).

~4:30pm | Finish & Optional Pub
We finish in Winchester town with an optional stop at one of our favourites - The King Alfred Pub 🍺🎈, where we’ve reserved a space in the beer garden for post-hike celebrations. The station is a short (10-minute) walk away if you’re heading back to London. The hike officially ends here, and participants are responsible for their onward travel.

• Guided hike with Waypoint Crew
• Qualified Lowland Leaders
• A great crew of like-minded outdoorsy legends

• Travel to/from Winchester
• Picnic lunch + snacks
• Pub drinks, food & refreshments

Consent Form

As part of signing up for this event, you'll be required to complete a consent form and provide details of any medical conditions. This will be included within the Eventbrite registration process.

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Refund Policy

Refunds will only be given if the event is cancelled. If you can no longer attend, you’re more than welcome to sell your ticket to someone else; however, please email us if you do so.

Terms & Conditions

By signing up for this event, you are agreeing to our Terms & Conditions. This event is for over-18s only.

If you have any other questions, please feel free to get in touch with us via [email protected].

Can’t wait to see you all there!

Waypoint Crew :)

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