About this Event
Waypoint Escape: 23km Hastings to Rye Coastal Hike & Pub (Ages: 20's - 40's)
Waypoint is London’s close-knit, adventure-loving crew for like-minded legends (20's - 40's). Big hikes, belly laughs, post-walk pints - and pushing yourself a little further each time.
Get ready for a proper coastal adventure along one of the most beautiful stretches of coastline in the South East. Starting at Hastings Station, we’ll climb up onto the cliffs beside the historic cliff railway before following rolling coastal paths, woodland trails, and steep hills with stunning views over the English Channel.
After a few hours, we’ll reach Fairlight Cove and head inland through quiet lanes and farmland before our main break on the wild stretch of Pett Level Beach. From there, we follow peaceful paths along the Royal Military Canal and climb to the medieval town of Winchelsea for a coffee stop.
The final stretch takes us through open countryside past Camber Castle before arriving in the cobbled streets of Rye, where we’ll celebrate the day with a well-earned drinks at the Ypres Castle Inn. 🍻
🗓️ Event Details
- Date: Sunday 31st May, 2026
- Meet: 10:15am at Hastings Station
- Start: 10:35am sharp
- Finish: Around 6:30pm in Rye
- Optional Pub Stop: Ypres Castle Inn, Rye (10-minute walk from station)
- Distance: 23km / 14.2 miles
- Time: About 8 hours total (7 hiking + breaks)
- Grade: Moderate – longer distance with several steep climbs early in the hike
- Route: Point-to-point (Hastings → Rye)
🥾 Your Guide
Marcela – Adventurous soul who loves hiking, wild camping, scrambling, skiing, swimming, cycling, kayaking, horse riding, archery… and more. Based in London, she’s always chasing the outdoors or planning trips abroad. A qualified guide, she hosts hikes and adventure trips overseas. Dreamer, funny, confident, and a little stubborn - always up for a challenge.
Beth - Founder of Waypoint Crew and qualified Lowland Leader. Loves big countryside days that end with a cold pint and good company.
🕙 Rough Schedule
- 10:15am – Meet at Hastings Station (There is a train arriving at 10:10am from London )
- 10:35am – Set off (running late? Ping the WhatsApp group)
- Break 1 – Scenic cliff-top break (~15 mins)
- Break 2 – Main beach stop at Pett Level Beach (~30 mins)
- Break 3 – Coffee stop in Winchelsea (~15–20 mins)
- 6:30pm (onwards) The hike officially finishes in Rye town centre. We have optional celebratory drinks at the Ypres Castle Inn before the train home.
✅ Included
- Guided hike with Waypoint Crew
- Qualified Lowland Leader
- A great crew of fellow outdoor enthusiasts
❌ Not Included
- Travel to/from Hastings/Rye
- Picnic lunch and snacks
- Drinks and pub food
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.
Photography & Videography Consent
Photographers and videographers may join this event. By signing up, you consent to the use of your photos and videos captured during the day for marketing and promotional purposes.
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 :)
Follow us on Instagram!
Event Venue & Nearby Stays
Station Approach, Station Approach, Hastings, United Kingdom
GBP 26.71 to GBP 28.88
