Explore Portland Differently
Discover somewhere new - or rediscover somewhere you thought you knew.

- Follow a carefully planned self-guided route through the area
- Use real landmarks and features to crack around 18 clever clues
- Notice fascinating features you'd normally walk straight past
- Great fun for everyone from 6 to 106
- Around 3.5 hours of exploring
Around 3 miles of walking - One trail is perfect for up to 5 people
How it Works
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1. Choose how you want to explore
Use the App, print your Trail at home, or let us print and post it to you.
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2. Access it
instantlyYour App and PDF are ready immediately, whichever option you choose.
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3. Explore
& solveFollow the route and crack the sneaky clues along the way.
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4. Submit
your answerEnter your final
answer online to
reveal the ending.
Great detectives needed!
A mystery is waiting to be solved in
Portland
Walter Plank, Portland's well-known mackerel catcher, had turned his fishing boat, The Hook, Line & Sinker, into a racing yacht, much to the dismay of the local sailor Godfrey Scuttlebutt and his yacht owning chums. But when Walter's yacht was discovered abandoned in the harbour, it was clear that something was amiss. Could Scuttlebutt have had a hand in this strange disappearance?
Join Chief Rowan Boats and his team of top detectives as they dive into this thrilling water-themed scavenger hunt around Portland. As you follow the Trail route, you'll uncover sneaky clues hidden on existing buildings, permanent features, and landmarks, all while enjoying a fun day out with family and friends.
Get ready to set sail on an adventure through Portland's Academy and Castle as you solve the mystery of the missing yacht!
Water Palaver in Portland
Are you looking for something to do with family and friends or seeking a fun day out with the kids in Portland? Then why not explore Portland on this self-guided Detective Mystery Trail that will take you on a scavenger hunt through the town's top landmarks and attractions.
Your adventure begins at the famous Olympic Sailing Academy, where you'll uncover clues to help you solve the case. From there, you'll journey through the Portland Marina, Portland Castle, and Chesil Beach, before returning along the scenic Beach Road.
Get ready to dive into the mystery and reveal the truth about Walter Plank's strange disappearance!
Every clue brings you closer to the truth...
Piece together the evidence, identify the culprit and discover how the case ends.
Trail Information
Trail Information
Trail Location
The Portland Island - Castle & Chesil Beach Treasure Trail starts at:
National Sailing Academy
Hamm Beach Road
Portland
Dorset
DT5 1SA
England
Trail Details:
- A Detective Mystery themed walking Treasure Trail around Portland Island
- Ideal for discovering more about where you live or exploring somewhere new
- Trails are done in your own time at your own pace
- This Trail involves approximately 3 miles of walking and will take around 3.5 hours to complete
- This Trail is suitable for all ages from 6 - 106 (no children necessary!)
- One Trail booklet is enough for 4-5 people
- Circular 'loop' Trail route
- Mobile phone text service for clue answers if you get stuck, ensuring that no mystery goes unsolved
- This Trail can be sent to you in the post or downloaded today for instant Trailing fun!
More Information:
Before you embark on your intriguing investigation around Portland, here are a few handy tips…
Easy to Navigate – This is a scenic but challenging route. While parts are suitable for pushchairs, Portland is famous for its hills and there are several steep uphill and downhill sections along the way, plus some gravelly and pebbly paths near Chesil Beach. Comfortable footwear is strongly recommended.
Bring Your Furry Sidekicks – Dogs are welcome to join the case. Much of the Trail follows pavements and coastal paths, with open areas near Chesil Beach for fresh-air sniffing. Please keep dogs under control, especially near roads and busy marina areas, and check any local bylaws before letting them off the lead.
Parking Sorted! – Parking is available at the Weymouth & Portland National Sailing Academy (DT5 1SA), right by the start point. If this car park is full, head instead to the car park near Portland Castle (DT5 1AZ) and begin the Trail at Clue 07, looping back later to collect the earlier clues.
Need the Loo? – There are no public toilets directly on the route. However:
The café at Clue 14 has facilities for customers - a garage and supermarket further along the route also have toilets.
Want to Make a Day of It?
Discover Portland’s Story – Take time to explore Portland Castle, Henry VIII’s coastal stronghold, or visit the Weymouth & Portland National Sailing Academy to see where Olympic sailors train.
Coastal Curiosities – Chesil Beach is one of Dorset’s most famous natural landmarks. Stretching for 18 miles, its unique shingle has inspired smugglers, scientists and writers alike.
Refuel with a View – There are several cafés and pubs along the way, perfect for a well-earned cuppa or lunch stop after cracking a few clues.
Mini Detective Club
Mini Detective Club
We have three super duper themed Clubs for your child to enjoy as part of their Treasure Trail experience.
Perfect for 4-8 year olds, the concept behind the Clubs is that your child will get a bundle of goodies to excite
them about their forthcoming Trail experience, something to keep them entertained whilst travelling to and from
the Trail, and something to be given on completion of the Trail as a keepsake.
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What is a Treasure Trail?
What is a Treasure Trail?
