What’s On in Kent This May: Festivals, Food, Bluebells and a Royal Jousting Anniversary to Look Forward To

May is shaping up to be one of the busiest months in Kent’s events calendar, with a packed programme of food festivals, craft fairs, vintage transport celebrations, live music and outdoor adventures spread across the county. With the weather having been kind to outdoor events in recent weeks, here is your essential guide to what’s on across the Garden of England this month — and one major summer attraction already on the radar.

Already Under Way: Weald of Kent Country Craft & Food Show at Penshurst Place

2–4 May | Penshurst Place, Tonbridge, TN11 8DH | 10am–5pm daily

If you haven’t already been, the long Bank Holiday weekend brought one of Kent’s most popular outdoor events to the grounds of Penshurst Place. The Weald of Kent Country Craft & Food Show, running from Saturday 2 May to Bank Holiday Monday 4 May, features more than 175 independent stallholders spread across six indoor marquees and outdoor markets. Visitors can browse handmade jewellery, homeware, clothing, artwork, health and wellness products, and artisan food and drink.

Entertainment includes a free-flying falconry display, traditional fairground rides, live music and craft demonstrations from skilled artisans showcasing traditional British crafts including blacksmithing, basketry, willow-weaving and woodcarving. Children under 16 enter free when accompanied by an adult, and the estate’s own Adventure Playground is included in the admission price. Penshurst Place itself — with its magnificent medieval house and award-winning gardens — can also be explored separately during the event.

Running alongside the show on 3–4 May, Camp Wilderness’ bushcraft experts are on site at the Woodland Trail offering children axe-throwing, archery, campfire cooking and camouflage challenges — all included with standard admission.

Tenterden Food & Drink Festival — 10th Anniversary

8–10 May | Tenterden Recreation Ground, off High Street, TN30 6RA
Fri: 12pm–6pm | Sat: 9am–7pm | Sun: 10am–5pm

One of the most eagerly anticipated food events in the Kentish calendar, the Tenterden Food & Drink Festival returns to the Recreation Ground this weekend, now celebrating its 10th anniversary. Held in the historic market town often called the “Jewel of the Weald,” the festival brings together a broad selection of local, national and international food and drink stalls across three days.

Visitors can enjoy al fresco dining from a wide variety of world street food vendors, and drinks from what the organisers call the “bars of distinction”. Live music runs throughout the weekend, and the event is family-friendly — well-behaved dogs on leads are also welcome. Stalls include artisan cheese, fresh produce, international cuisines and regional Kent specialities. Traders include the likes of Stuff & Bite Food Group serving fresh Pad Thai and other authentic Thai street food alongside many others. The festival also has a comedy evening on one of the nights — tickets for that element are sold separately through the Zoom Events website.

Tenterden town centre’s independent shops and cafés are a short walk from the Recreation Ground, making it a full day out in one of Kent’s most characterful towns.

Canterbury Wine Festival

Fri 15 May (VIP) & Sat 16 May | Westgate Hall, 3 Westgate Hall Road, Canterbury CT1 2BT

Kent has quietly become one of England’s most exciting wine regions, and the Canterbury Wine Festival — now in its established place on the annual calendar — is the county’s flagship showcase for its vineyards. The two-day event at Westgate Hall in the heart of Canterbury offers visitors the chance to taste more than 70 different Kent wines and meet the producers behind them.

Participating vineyards include many of the county’s most celebrated names: Balfour, Biddenden, Gusbourne, Chapel Down, Simpsons Wine Estate, Domaine Evremond and many more — from large award-winning operations to smaller family estates. New for 2026 is a VIP Experience on the Friday evening (15 May, 7–10pm), which includes exclusive early access to the festival, a Masterclass led by Master of Wine Clive Barlow, food pairing and a goody bag — all within the ticket price. The Saturday session (12pm–7pm) offers the standard Festival Experience with over 60 wine tastings and a brochure.

Add-on Masterclass sessions, cheese platters, oysters and pizza are available to purchase on the day. The venue is fully accessible, close to transport links and a short walk from Canterbury West station. This is an 18+ event.

Faversham Festival of Transport

16–17 May | Faversham Town Centre | 10am–4pm | Free Entry

One of the most popular free events in north Kent, the Faversham Festival of Transport takes over the historic town centre for a two-day celebration of vehicles from across the decades. Attracting around 5,000 visitors each year, the event fills Faversham’s beautiful Market Place, Court Street, Preston Street and Standard Quay with vintage cars, buses, motorcycles, military vehicles and steam engines.

Saturday is all about the free vintage bus rides — a hugely popular feature that takes passengers on scenic routes around Faversham and the surrounding villages. Buses depart from outside the ASK Italian restaurant on Court Street. Saturday also sees Preston Street home to the Best of Faversham Market and an Eventissima artisan market at the Alexander Centre, packed with locally made goods from Faversham’s makers, designers and growers. The oldest market in Kent — Faversham Charter Market — also trades as usual.

Sunday is the main car and motorcycle show, with steam vehicles arriving in convoy and hundreds of exhibiting vehicles parading along Preston Street. South East Coachworks holds transport-related activities including bus memorabilia on Saturday and remote-control trucks and converted bus displays on Sunday. A park-and-ride service operates from Macknade on both days.

Kent Food Fest at Knockholt

Saturday 16 May | Knockholt, TN14 7PH | from 12pm

For those unable to make Tenterden the weekend before, the Kent Food Fest at Knockholt offers another opportunity to sample local produce and street food. Located in a picturesque area of the North Downs near Sevenoaks, this is a solid family-friendly outdoor food event.

Walking Tour: A Day on the Kent Coast

Tuesday 19 May | Dover Priory Station | 11:30am

For those who prefer their entertainment to come with fresh sea air, a guided walking tour along the Kent coast departs from Dover Priory Station on Tuesday 19 May. This is a great way to explore one of the most historically significant stretches of coastline in Britain, with the iconic white cliffs providing a dramatic backdrop.

Kent Tribute Festival at Quex Park

22–24 May | Quex Park, Birchington, Thanet

The Kent Tribute Festival returns to the beautiful grounds of Quex Park in Birchington for a full weekend celebration of live tribute music. Showcasing some of the best tribute artists from across the UK and Europe, the festival is family-friendly and also offers family camping for those who want to make a full weekend of it. Quex Park — a country estate in the heart of Thanet — provides a stunning backdrop for the event. Tickets should be booked in advance.

Neolithic Trail Walk from Aylesford

Sunday 24 May | Aylesford Railway Station | 9:30am

History enthusiasts and walkers can join the Neolithic Trail walk departing from Aylesford station on the last Sunday of the month. The Medway valley contains some of the most significant prehistoric monuments in England, including the famous Kit’s Coty megalithic burial chambers, and this walk connects several of those ancient sites.

Lovebox at Dreamland, Margate

29–30 May | Dreamland, Hall by the Sea Road, Margate CT9 1XJ | 18+

One of London’s most iconic music festivals finds a new seaside home at Dreamland in Margate at the end of the month. Lovebox — which built its reputation over decades as a cornerstone of the London summer festival scene — makes its debut at the Margate seafront amusement park across two stages: the outdoor Scenic Stage and the indoor Hall by the Sea.

The 2026 lineup brings together artists who shaped the original Lovebox story alongside fresh faces. Confirmed artists include Rudimental, Soul II Soul, Jayda G, Scissor Sisters, Friendly Fires, Horse Meat Disco, Goldie b2b Special Request, 4AM KRU and Girls Don’t Sync. This is an 18+ standing event. Re-entry is not permitted. Accessible and companion tickets are available via AXS. Tickets are available through the Dreamland website.

Kent Card Show at Detling

30–31 May | Detling Showground, Maidstone | 9am

Sports and trading card collectors should note the Kent Card Show at Detling Showground on the final weekend of the month. Vendor tables and trading opportunities make this a popular gathering for enthusiasts across the county.

Nature’s Own Show: Bluebell Season in Kent’s Woodlands

This year has delivered an exceptional — and unusually early — bluebell season across Kent, with flowers emerging weeks ahead of schedule thanks to a mild winter and warm spring. Hole Park Gardens in Rolvenden made national news in late March when it recorded its earliest-ever spring opening, with blooms described as arriving at the fastest rate the estate had seen in its long history of record-keeping.

While peak bluebell season in north-west Kent typically falls between mid-April and early May, the blooms tend to persist a little longer in more sheltered or elevated woodland sites, and some spots across the county still had bluebells “in full bloom” as recently as 4 May. If you’re yet to see them, early May remains worthwhile in the right locations.

The best remaining spots to check this week include:

• Hole Park Gardens, Rolvenden (near Cranbrook, TN17 4JA) — one of the finest private bluebell gardens in the South East, open 11am–6pm, normal admission fees apply
• King’s Wood near Chilham — an ancient forest offering a breathtaking blue carpet; walkers start from the cobbled square in Chilham village
• Meenfield Wood, Shoreham — high on the North Downs ridge, described as having “long-distance swathes of cobalt beneath stately oaks” and usually the least crowded of the notable spots
• Newyears Wood / Birches Croft, Cudham — another secluded North Downs location that regularly features in the county’s top bluebell rankings
• Andrew’s Wood, between Halstead and Shoreham — accessible from a small car park, with particularly good displays on the east-facing slopes of a dry valley

Always check local social media or the Hole Park “Bluebell Barometer” on their website before travelling, as conditions change quickly.

On the Horizon: Hever Castle Jousting — 40th Anniversary Season (July–August)

While the jousting is not a May event, it deserves an early mention for forward planning. This summer, Hever Castle will mark a significant milestone as its famous jousting tournaments — presented by the Knights of Royal England — celebrate their 40th anniversary season.

To mark the occasion, Hever has introduced an entirely new theme: Battle of the Queens — a light-hearted narrative inspired by two of the castle’s most celebrated Tudor figures, Anne Boleyn and Anne of Cleves. New heraldic livery, vibrant costumes and horse embellishments have been designed for the season — the first costume refresh at Hever since 2012.

Reaching 40 years of joust is a fantastic milestone — Duncan Leslie, CEO, Hever Castle.

The jousting calendar runs on selected weekends from July through to the end of August: 11, 12, 18, 19 and 24–26 July, and 8, 9, 15, 16, 22, 23 and 28–31 August. Tournaments begin at 2:15pm with the castle forecourt procession, with approximately 90 minutes of action including stunt riding, choreographed medieval battles, galloping horses and professional commentary. The jousting is included within standard castle admission. Hever Castle is located at Hever, Edenbridge, TN8 7NG.

Also Running Throughout May

• Ocean Photographer of the Year Exhibition — The Historic Dockyard, Chatham, ME4 4TZ. Running until 31 August, this exhibition showcases stunning marine photography from around the world. Entry is included in standard Dockyard admission.
• Active Walking Month in Faversham — throughout May, a programme of walking routes and exploration activities centred on the historic town encourages residents and visitors to explore Faversham on foot.
• Faversham Alexander Centre Artisan Markets — the first and third Saturday of every month, the Alexander Centre on Preston Street hosts artisan craft markets.

Always check individual event websites for the latest information on tickets, timings and any last-minute changes before travelling. Details correct at time of publication.

Sources

• Penshurst Place — official events listing
• ICHF Events — Weald of Kent Country Craft Show 2026
• Tenterden Food & Drink Festival — official site
• Canterbury Wine Festival — Westgate Hall
• Faversham Town Council — Festival of Transport
• Dreamland Margate — Lovebox 2026
• Visit Thanet — Quex Park & Lovebox listings
• Hever Castle — Jousting 2026
• Hole Park Gardens — Bluebell Spectacular & Bluebell Barometer
• The Historic Dockyard Chatham — Ocean Photographer of the Year Exhibition