5

Walking groups

Aggregated across Maidstone

  • Providers1
  • Median priceNot listed
  • Format5 in-person
  • Updated23 Jul 2026
  • Directory93,000+ activities UK-wide · All ages

Walking in Maidstone

5 bookable walking groups in Maidstone from 1 provider including Boots On Adventures. Last updated 23 July 2026.

5 walking classes · 1 providers

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Showing 5 of 5 walking groups

Walking

Boots On Adventures

All ages
📅 2 Sep 2026
📍 ME17 1DP · Medway postcode area

Join us on this relaxing weekday guided walk exploring the beautiful countryside between Ulcombe and Sutton Valence. Starting in the peaceful village of Ulcombe, this circular route follows sections of the renowned Greensand Way, taking in rolling farmland, ancient woodland, and some of the finest panoramic views across the Kent Weald.

Walking

Boots On Adventures

All ages
📍 ME17 1HU · Medway postcode area

On the 25th of March 2026 we will be strolling from Harrietsham, exploring the surrounding countryside of the North Downs along ancient routes and woodland paths as a part of Heart of Kent Walking Festival.

Walking

Boots On Adventures

All ages
📍 CT5 1AW · Canterbury postcode area

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.

Boots On Adventures
Walking

Boots On Adventures

18+
📅 22 Aug 2026
📍 ME15 6YE · Medway postcode area

Discover a different side of Maidstone on this relaxed historical pub tour led by Ben, where local stories, characters, and centuries of brewing heritage come to life. This is a chance to step into pubs once visited by figures like Charles Dickens and Samuel Pepys, explore hidden corners of the town’s past, and enjoy the atmosphere of Maidstone’s most characterful drinking spots. As we wander between four historic pubs, you’ll hear tales of old breweries that once dominated the town, ghostly encounters with cavalier soldiers, mischievous Victorian children, wartime airmen blaming “Gremlins,” and even a few scandalous politicians. With plenty of time to sample beer, wine, gin, or your drink of choice, this tour blends history and hospitality into a fun and memorable day out.

Boots On Adventures
Walking

Boots On Adventures

📅 30 Aug 2026
📍 ME14 3EY · Medway postcode area

Boots On Adventures Outdoor Skills Session Learn how to read a map, use a compass, and navigate with confidence in the Kent countryside. Join Boots On Adventures for a hands-on navigation skills session in Bredgar, Kent, designed specifically for adults who want to build confidence outdoors in a relaxed, supportive environment. 👉 Small group | Practical learning | No experience needed Location & Meeting Point Bredgar Village Hall Before heading to: Bredgar Farm Shop for a relaxed introduction (optional drinks available, not included), then out into the surrounding countryside for practical navigation training.

About these walking groups in Maidstone

Of the 5 venues shown here that list a postcode, 4 are in the Medway (ME) area and 1 in the Canterbury (CT) area.

Of the 5 venues shown here, we hold a listed price for all 5, an age range for 4, session times for none and a postcode for all 5.

Where a fact is not held we leave it out rather than estimate it — check with the provider before booking.

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