October Weekends in Scarborough - Free Night Offer
Book Friday & Saturday
Stay Thursday Night Free
October is a lovely time to stay in Scarborough — crisp sea air, quieter streets and that cosy autumn feel. With theatre, live music and coastal events throughout the month, it’s the perfect time to unwind by the sea. Scarborough Spa and the Stephen Joseph Theatre both have full October programmes, so pick the weekend that suits you, see what’s on, and enjoy an extra Thursday night on us. For full listings, click here for the Stephen Joseph Theatre (SJT) and here for the Scarborough Spa — and check out our top picks below.
Choose Your Weekend - Enjoy Thursday Night Free
Friday 2nd to Sunday 4th October
(Stay Thursday 1st Free)
Alan Ayckbourn’s latest world premiere The Trial of Romeo Oscar runs at the SJT until 3rd October, and on Friday 2nd October you can catch Sh!t‑Faced Shakespeare: Romeo & Juliet at Scarborough Spa — a brilliant mix of theatre and comedy to kick off your October weekend with us. Click the images below for more details.
Friday 9th to Sunday 11th October
(Stay Thursday 8th Free)
Jon Godber’s The Highwayman continues at the SJT — a strong autumn highlight — and on Saturday 10th you can also catch the brilliant improvised comedy of The Noise Next Door. Over at Scarborough Spa, The Bob Dylan Band perform on Friday 9th, followed by An Evening with Phoenix Nights on Saturday 10th. Plus, Scarborough Autumn Streets brings free outdoor performances and activities across the town centre all weekend.
Friday 16th to Sunday 18th October
(Stay Thursday 15th Free)
Scarborough Spa hosts a full weekend of live entertainment, with The Francis Rossi Songbook: Quo – Past, Present, Future Tour bringing a night of classic hits, and the Northern Soul Weekender running throughout the weekend. On Friday 16th, The Comedy Store on Tour delivers top‑tier stand‑up, and on Saturday 17th Sky Full of Stars brings an electrifying, authentic tribute to Coldplay.
Friday 23rd to Sunday 25th October - Our Closing Weekend Party
(Stay Thursday 22nd Free)
We’re wrapping up October — and our season — with a brilliant closing weekend. Scarborough Spa kicks things off on Thursday 22nd with The Wonder Stuff & Inspiral Carpets, two iconic bands sharing one huge night. Friday and Saturday night, Peasholm Park will once again be transformed into a wonderland of lanterns and illuminations for the biggest-ever Moonlight on the Lake. Then on Saturday evening, join us in the bar for live music right with the amazing Freddie Schmuck here at the hotel, a relaxed, friendly finale to round off your stay and celebrate the end of our season.
Ready to Book?
Ready to book? Questions? Simply give us a call on 01723 373717 and we’ll take care of everything.
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Terms & Conditions
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Offer applies to Friday & Saturday night stays in October 2026 only, the Thursday free night stay also includes breakfasts.
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New bookings only - existing bookings cannot be changed onto this offer.
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Free Thursday night applies as stated; no alternative night or discount is available
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Subject to availability.
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The Headlands Hotel reserves the right to withdraw the offer at anytime.
