Here are four seasonal events in or near Helmsley that you don't want to miss
There’s something extra special about Helmsley at Christmas — Just a short walk from Helmsley Meadows, our peaceful retreat is perfectly placed to enjoy it all. Whether you’re here for a weekend escape or a midweek stay wrapped in quiet countryside comfort, here’s what to look forward to this festive season.
✨ Helmsley Christmas Lights Switch-On
Friday 28 November 2025
Helmsley’s market square turns into a twinkling winter wonderland as the Christmas lights are switched on, officially marking the start of the festive season. It starts from 4:30pm, the square fills with laughter, music and the hum of conversation as locals and visitors gather for the countdown.
There’s usually live entertainment, Helmsley's town crier will be there, and there will be plenty of cheer as the town comes together beneath the sparkling canopy of lights. The switch-on itself takes place at 5:30pm, followed by more festivities — it’s the perfect way to feel part of Helmsley’s close-knit community.
(Tip: Arrive early to enjoy a wander around the independent shops before they close — many have their windows dressed beautifully for Christmas.)
👼 The Angels of Hope Christmas Tree Festival at All Saints’ Church
Saturday 29 November – Saturday 13 December
🕘 Open 9am–4pm Monday to Saturday, and noon–4pm on Sundays
Step inside All Saints’ Church and you’ll be greeted by a twinkling forest of Christmas trees over 20 of them — each one lovingly decorated by local groups, schools and businesses, all inspired by this year’s theme: Angels of Hope.
It’s free to visit, though donations go towards the church’s local and charitable work. A quiet moment here, surrounded by light and offers a peaceful pause in the midst of the festive bustle.
🏘️ The Helmsley Advent Window Trail
Throughout December
Each evening, from 1 December onwards, a new festive window is revealed somewhere in town — gradually creating a walking trail of 24 beautifully decorated displays by Christmas Eve.
It’s a gentle way to explore the town as day turns to dusk: wrap up warm, grab a hot chocolate from one of the cafés, and wander the streets in search of the next glowing window.
Every single one is crafted with care and community spirit. By mid-December, the whole town will become a living advent calendar, sparkling with local creativity.
🌈 Follow the Yellow Brick Road to Christmas at Castle Howard
Just a short drive from Helmsley, the magnificent Castle Howard is once again transforming for the festive season — and this year’s theme is “The Wizard of Oz.” Expect an enchanting journey through the grand rooms, where each space brings the story to life with dazzling decorations, immersive soundscapes and twinkling lights.
There are themed afternoon teas, festive trails for children, and of course, the famous Castle Howard Christmas trees that tower high beneath the painted ceilings.
It’s a truly unforgettable experience — Just remember to book early; tickets often sell out fast.
❄️ A Festive Stay to Remember
After a day of festive exploring, return to the warmth of Helmsley Meadows — light the wood burner, pour a glass of something comforting, and let the peace of the countryside wrap around you.
December is one of the most magical times to stay: quiet walks, starlit hot tubs, and the simple joy of slowing down.
Because here in Helmsley, Christmas isn’t about rushing — it’s about connection, light, and the gentle magic of time well spent.
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See you soon at Crossing Cottage at Helmsley Meadows, we can’t wait to welcome you!
Karen, Darren and Cody
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