Boots On Adventures

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Step into the shadows of Whitstable’s past and discover a side of the town that few ever truly see. This guided historical pub tour blends storytelling, seaside charm, and a lively social atmosphere as we explore centuries of intrigue, smuggling, and local legend hidden behind pub doors and along quiet streets.
Starting from Whitstable Harbour, just a five-minute walk from Whitstable Station, this relaxed four-hour experience takes you through the heart of the town, stopping at five historic pubs where history and hospitality go hand in hand.
As we wander through Whitstable’s streets and along its shoreline, we follow in the footsteps of Romans, smugglers, and generations of locals who have shaped its unique identity. Along the way, you’ll have the chance to enjoy a drink (not included) at each stop while soaking up the atmosphere and stories that bring these places to life.
The walk finishes at the sea wall outside the Whitstable Oyster Company just a short walk from our starting location.

Cost: £15 (does not include any drinks you might purchase during this tour)
Meet and Start Time: 12:45 meet for 13:00 start
Walking time: 3.5/4 hrs
Walk Leader: Ben Crozier / Ian Henderson
Location
Meeting point: Next to The Old, Harbour Office, Whitstable Harbour, Whitstable CT5 1AB
Finishing point: Horsebridge Rd, Whitstable CT5 1BU
what3words: ///pupils.whisk.oblige
Car Parking: Charges not included
Route
Terrain: On the streets and seafront of Whitstable
Distance: Approximately 2 miles
Walk Type: Linear

Ale, oysters and old tales: a historic Whitstable pub walk — Discover the Stories Behind the Town’s Most Characterful Pubs
Join us for a relaxed and sociable walking tour through Whitstable’s historic pubs, where coastal heritage, colourful characters, and centuries of local stories come together along one of Kent’s most distinctive seaside towns.
Starting from just outside Whitstable Harbour, just a five-minute walk from Whitstable Station, we’ll wander through the town and along the shoreline, visiting five carefully selected historic pubs. Each stop has been chosen for its atmosphere, character, and connection to Whitstable’s past, from traditional drinking spots shaped by the fishing trade to long-standing favourites linked to the town’s smuggling history.
Along the way, you’ll hear a mix of fascinating and entertaining stories drawn from Whitstable’s past. Expect tales of Romans and smugglers, a famously polite horror actor with local ties, forgetful gangsters whose plans didn’t quite go to plan, and an Archbishop whose story ended in a particularly grim way involving bones. These stories, both light-hearted and darker in tone, help bring the town’s history vividly to life.
This guided experience is designed to be easy-paced, informative, and social, with plenty of time to enjoy a drink at each stop if you choose. The route takes in both the characterful streets and the seafront, reaching the sea wall outside the Whitstable Oyster.
Perfect for those who enjoy local history, traditional pubs, and a relaxed group atmosphere, this walk offers a unique and entertaining way to experience Whitstable from a different perspective.
A memorable afternoon of history, storytelling, and good company, set against the backdrop of one of Kent’s most loved coastal towns.
The tour starts promptly on time. If you’re running a bit behind, please give us a call to let us know .

Important Notes
We do not encourage or condone driving under the influence. By participating in our tours, you agree to respect local laws and prioritize the safety of yourself and others by securing non-driving transport.
We take photos during our walks for promotional and training purposes. If you prefer not to be included, just let us know on the day.
Cancellation policy states: Full payment becomes due if a user cancels within 7 days of the activity. Any person cancelling outside of 7 days, will receive a credit available to use within 90 days. Cancel at least 7 days before the event to receive a credit note for a future walk, valid for 90 days.
This event is not suitable for under 18s.
Please note that this is a tour and not included in loyalty cards discounts.

To book paying deposit via website

Journey deep into Kent’s ancient landscape on a two-day guided adventure along the legendary Neolithic Trail. This immersive walk around the Medway Megaliths brings you face to face with some of Britain’s most mysterious prehistoric sites—places where stories, legends and landscape intertwine.
Across rolling hills, timeless trails, and sweeping views of the Kent Downs National Landscape, you’ll explore ancient routes such as the North Downs Way, Pilgrims Way, and the Medway Valley Walk. Along the way, you’ll stand before remarkable sites including Kits Coty, Little Kits Coty, the White Horse Stone and Coldrum Long Barrow—each carrying its own echo of the past.
As daylight fades, you’ll settle into a peaceful campsite perched on the North Downs Way. Enjoy a hearty home-cooked dinner prepared in Dutch ovens over an open fire, indulge in campfire treats, and watch the sun melt into the horizon. It’s a rare moment of stillness—a chance to experience this ancient landscape as it once was.
This journey blends natural beauty, historic discovery, and meaningful adventure. From panoramic viewpoints to ancient footpaths still alive with stories, the Neolithic Trail offers an experience that stays with you long after the weekend ends.

Schedule

Date: 24–25 May 2026
Meet & Start Time: 10:00am
Expected Finish Time: Around 4:00pm
Your Guides: Ian Henderson & Ben Crozier Location

Meeting Point: Aylesford Train Station
what3words: ///admire.roses.erupt
Car Parking: Charges apply (not included)
Route Details
Terrain: Mixed pathways, trails & countryside
Distance: Two days covering approx. 17.5 km (11 miles)
Walk Type: Circular route

How Your Days Will Unfold
Day One – Aylesford to the North Downs
Your adventure begins at Aylesford Station, where your bags are collected to keep your walk light and enjoyable.
From here, you follow a network of ancient pathways used for thousands of years—routes travelled by Neolithic communities, medieval pilgrims, and generations of local storytellers. The trail leads you through charming town streets and onward to some of the most significant prehistoric sites in Britain. Along the journey, your guide shares insights into the myths, archaeology, and people who shaped this landscape.
As late afternoon arrives, you reach a unique, sustainable farm campsite nestled along the North Downs Way. Here you can relax, explore, or simply take in the view while dinner simmers over the fire. The evening is spent around the campfire, sharing stories as the sun sets across the valley.
Day Two – Dawn Light and Ancient Footsteps
Wake to a hearty breakfast and the smell of morning air rolling off the Downs. With renewed energy, you continue your pilgrimage across the Kent Downs National Landscape, passing historic monasteries, ancient churches, manor parks, and iconic Neolithic monuments.
After a final stretch of beautiful countryside walking, the trail leads you back to Aylesford Station, where your bags are waiting for you and your weekend journey comes full circle.
Learn More About the Neolithic Trail Kent Adventure
Picture the early morning light spilling across the Medway Megaliths—vast stones casting long shadows that hint at thousands of years of human history. Stand still for a moment and you can almost feel the presence of those who walked these paths long before us.
During this two-day adventure, you’ll follow routes shaped over millennia, exploring landscapes that have carried the footsteps of Neolithic communities, Roman settlers, medieval pilgrims travelling toward Canterbury, and generations of travellers drawn to the beauty of the Kent Downs.
But this experience is more than a walk.

It’s a chance to immerse yourself in a living landscape.
Your history walk leader, Ben Crozier, brings each location to life with expert storytelling—revealing rituals, daily life, burial traditions, and the theories surrounding these awe-inspiring structures. As you stand before chambered tombs and megalithic stones, you’ll hear the ideas behind their construction and purpose, from spiritual significance to astronomical alignment.

What Awaits You:
Scenery That Tells a Story

Journey through open countryside, wooded trails, and sweeping ridgelines where every turn reveals a new perspective on this ancient land.
Megalithic Marvels

Visit powerful Neolithic monuments whose meaning still sparks debate and wonder. See the stones. Feel their scale. Decide for yourself what they may have meant.
Stories That Bring the Past Alive

Learn about the people who shaped this place—from prehistoric builders to medieval monks and travelling pilgrims—through engaging, expert-led interpretation.
A Night Beneath the Stars

Experience the landscape as our ancestors once did. No bright lights. No rush. Just the glow of the campfire, the sound of the wind across the hills, and a sky full of stars.
A Weekend That Stays With You

From scenic trails to ancient mysteries, from shared stories to quiet moments in nature, this adventure offers something truly special. Many walks highlight history or landscapes. This one weaves them together into a weekend you’ll never forget.

Riverside wildlife and local heritage: Maidstone River Park anniversary walk
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Join us on Thursday 28th May 2026 for a special evening nature walk celebrating the 25th anniversary of Maidstone River Park, in support of Maidstone Borough Council. Starting from Allington Car Park on Castle Road, this relaxed guided walk follows the River Medway, exploring the rich natural habitats and green spaces that make this area so special.
As we set out along the riverside, the route offers a chance to slow down and take in the surrounding environment, with plenty of opportunities to observe local wildlife and seasonal changes in the landscape. The walk continues through Aylesford before entering Cobtree Manor Park, once the site of Maidstone Zoo, where open parkland and woodland provide a varied and interesting setting.
From here we continue through Allington Docks before looping back towards our starting point. This walk is ideal for those who enjoy gentle exploration, learning about local nature, and celebrating an important milestone for Maidstone’s green spaces.
Learn more about this wonderful walk:
Mark the 25th anniversary of Maidstone River Park with a guided evening walk that explores the natural beauty and heritage of the River Medway corridor. Led by the experienced Boots on Adventures team, this 5.7-mile circular route offers a relaxed and informative journey through one of Maidstone’s most valued green spaces.

Schedule

Date: 28 May 2026
Meet and Start Time: 06:00 meet for 06:15 pm start
Walking time: 3.15 hrs (incl. short break)
Staff Member: Ian Henderson
Location

Meeting point: Car Park at Castle Rd, Allington, Maidstone ME16 0NH
what3words: ///burst.salads.driver
Car Parking: Charges not included
Route

Terrain: undulates slightly throughout the trail
Distance: Approximately 9.5 km (6 miles)
Walk Type: Circular
Starting from Allington Car Park on Castle Road, the walk follows the River Medway, a defining feature of the local landscape that supports a wide range of wildlife. As we move along the riverside paths, there will be time to pause and observe the natural surroundings, from birdlife along the water to the changing plant life that lines the route.

The walk continues towards Aylesford, where the character of the landscape begins to shift, blending riverside scenery with village surroundings. From here we enter Cobtree Manor Park, a historic estate that was once home to Maidstone Zoo. Today, the park offers a peaceful setting of open grassland, mature trees, and managed habitats that support a variety of species.
As we continue through the park and beyond, the route leads into Allington Docks, where the working river environment provides a contrast to the quieter green spaces earlier in the walk. This mix of natural and industrial heritage helps tell the broader story of how the River Medway has shaped the area over time.
Throughout the walk, there will be a focus on the nature that thrives within this corridor, highlighting the importance of these green spaces for both wildlife and the local community. The pace is steady and sociable, allowing time to take in the surroundings and enjoy the experience as a group.