October is a particularly good month to spend a few days in Windsor.
The summer crowds have eased, the town starts to take on an autumn feel, and the events calendar gives you plenty of reasons to stay beyond a quick visit to Windsor Castle.
There is live music, theatre, family entertainment, Halloween experiences, local markets and cultural events happening across the town. You can spend a morning exploring the Castle and the Long Walk, find somewhere good for lunch, head to an afternoon event and finish the evening at the theatre or out for dinner.
And if you are visiting with children, October half term brings another reason to make a proper weekend of it.
So, if you are looking for things to do in Windsor in October 2026, here are some of the events and experiences worth putting on your list.
25 September – 18 October 2026
If you usually think of Windsor as a place for royal history, grand buildings and traditional sightseeing, the Windsor Fringe is a good reason to see another side of the town.
Running from late September into October, the festival brings together performances, music, workshops, walks and community events in venues across Windsor.
There are plenty of individual events to choose from, but a few that caught our eye include:
It is a useful reminder that Windsor has a cultural side that is easy to miss if you only stick to the main tourist attractions.
If you are planning an October weekend, have a look through the Windsor Fringe programme before you arrive. You may find something completely different from what you originally had in mind.
9-10th October 2026
An Oktoberfest in Windsor?
It is probably not the first thing that comes to mind when you think of the town, which is exactly what makes this one interesting.
For the first time, Royal Windsor Racecourse is hosting an Oktoberfest weekend, with Bavarian food, live music, dancing, steins and traditional games.
Expect the sort of atmosphere you would associate with Oktoberfest, including yodelling, stein holding and plenty of opportunities to get involved rather than simply sitting and watching.
It is a very different Windsor experience from spending the day around the Castle.
You could explore Windsor during the day, have dinner in town and then head to the racecourse for an evening of Bavarian food, music and entertainment.
If you are travelling with friends or as a group, this could make a particularly good reason to plan an overnight stay rather than trying to fit everything into one day.
Oktoberfest at Royal Windsor Racecourse
Brick or Treat at LEGOLAND Windsor
For families, October brings one of the biggest seasonal events at LEGOLAND Windsor: Brick or Treat.
The Halloween event takes place on selected dates from 10th October through 1 November, including the October half term period.
Expect Halloween themed entertainment, LEGO characters, spooky activities, live shows, rides and plenty of opportunities for children to get involved.
It also gives families another good reason to consider staying in Windsor rather than treating LEGOLAND as a standalone day trip.
After a full day of rides and Halloween activities, it is much nicer to have somewhere comfortable to return to, especially when travelling with children.
Windsor also gives you the option of combining LEGOLAND with other things during your stay. One day could be spent at the resort, while another could include Windsor Castle, the Long Walk, Eton and some of the town’s restaurants and independent shops.
That turns a theme park visit into a proper family break.
LEGOLAND Windsor – Brick or Treat
Neverland: The Peter Pan Drone Light Show
There is also something a little different happening at Royal Windsor Racecourse on 3 October.
Neverland: The Peter Pan Drone Light Show brings Peter Pan, Wendy and Tinker Bell into the night sky in a show inspired by J.M. Barrie’s classic story.
It is the kind of experience that can easily become the evening highlight of a Windsor trip.
Rather than spending another evening simply going back to your accommodation after dinner, you can build your day around it.
Spend the afternoon exploring Windsor and Eton, have an early dinner and then head to the racecourse for the evening.
For families, it is an obvious choice. But it could also work for couples or anyone looking for something different from the usual Windsor sightseeing itinerary.
Royal Windsor Racecourse – Neverland / Peter Pan Drone Light Show
October is also a good month for a theatre break.
Theatre Royal Windsor has a varied programme throughout the month, which means you can pair a show with dinner and turn an ordinary evening into part of your Windsor weekend.
The October 2026 programme includes:
12–17 October
Agatha Christie’s famous murder mystery comes to Windsor as part of its 75th Anniversary Tour.
18 October
A full evening of Motown classics, live music and dancing.
20–24 October
A psychological ghost story based on Henry James’s famous novella, making this an especially fitting choice as Halloween approaches.
27–31 October
A theatrical adaptation of the classic fairy tale, with performances running through the final week of October.
There are also other performances during the month, including WILKO: Love & Death ‘N’ Rock & Roll, Fastlove and The Anastasia File.
The theatre is right in the centre of Windsor, so it works particularly well as part of a simple evening itinerary:
Explore Windsor → dinner → theatre → walk back to your accommodation.
No complicated evening plans required.
Theatre Royal Windsor – What’s On
30-31 October 2026
If your idea of Halloween involves history rather than dressing up and collecting sweets, this one is worth knowing about.
Windsor: The Dark Side – Halloween Walking Tour takes visitors through some of the darker stories connected with the town.
The tour explores local legends, witches, royal tragedies, executions and ghost stories, giving you a very different perspective on a place that is usually associated with royal history and grand architecture.
Tours take place at 6.30pm and 8.30pm, starting outside Windsor Guildhall, and last around 1.5 hours.
It is an adults-only experience for those aged 16 and over.
The timing also makes it easy to build into an evening in Windsor. Have dinner beforehand, take the tour and then head back through the historic streets afterwards.
And if you have already spent the day looking at Windsor’s grander side, discovering some of its darker stories is a nice change of pace.
Windsor: The Dark Side – Halloween Walking Tour
Windsor is actually older than Windsor Castle.
The town dates back to the 7th century, with royal ownership probably established by the 9th century.
The original settlement was around three miles from the present town before it moved to its current location before 1110. It then became known as New Windsor.
So when you walk through Windsor’s streets today, you are not simply walking around a town that grew up around the Castle. There is a much older story underneath it.
It is one of those details that makes exploring the town on foot much more interesting.
The events above are some of the bigger reasons to visit, but you do not need to build your entire trip around organised events.
Some of the best parts of an October weekend in Windsor are much simpler.
Take a walk along the Long Walk and through Windsor Great Park. Explore the streets around the Castle and Guildhall. Cross Windsor Bridge and spend some time in Eton, where the atmosphere feels noticeably different from the busier centre of Windsor.
Stop for coffee. Browse independent shops. Find a restaurant for dinner. Walk beside the Thames.
And if the weather changes, you have plenty of indoor options, from the Castle and museums to cafés, restaurants and the Theatre Royal.
That flexibility is one of the reasons October works so well for a short break.
Visit Windsor – History of Windsor
Looking at the October calendar, it is easy to see why a day trip can feel a little rushed.
You could arrive in the morning, explore the Castle, have lunch, walk through Windsor and Eton, attend an afternoon event and still have a theatre performance or evening event waiting for you.
There is a lot to fit in.
Staying overnight gives you much more flexibility.
You can explore without constantly checking the time for the journey home. You can book a later dinner. You can attend an evening performance or Halloween tour. You can have a slow breakfast the following morning before heading out again.
And you do not necessarily need to stay in a traditional hotel.
Castle Properties offers a collection of serviced accommodation across Windsor and Eton, so there are different options depending on the size and style of your trip.
For larger families and groups, the Windsor houses offer the space of a home rather than a collection of separate hotel rooms.
Windsor Castle Townhouse sits just outside the Castle walls and offers five bedrooms, making it particularly useful for larger groups who want to stay right in the centre.
Church Lodge is another central four-bedroom option, with space for up to eight guests, a private courtyard garden and views towards Windsor Castle.
Windsor Castle House + Garden sits beside the Long Walk and offers four double bedrooms, 2.5 bathrooms, living and dining areas and a private garden.
For something with more of an Eton feel, the Silversmith Court apartments overlook Eton High Street and put you close to Eton College, the Thames and the walk across to Windsor.
There is also Western Cottage, a characterful Queen Anne property dating from 1702, right in the centre of Windsor.
The point is not that there is one perfect place to stay.
It is about finding a base that works for the way you want to experience Windsor.
If you are not sure how to put everything together, here is one way to approach it.
Friday evening
Arrive in Windsor, settle into your accommodation and head out for dinner.
Saturday morning
Explore Windsor Castle and take a walk along the Long Walk.
Saturday afternoon
Cross over to Eton, explore the High Street and stop somewhere for lunch or coffee.
Saturday evening
Choose your event. Depending on the weekend, that could mean Oktoberfest, a theatre performance, the Peter Pan drone show or another Windsor Fringe event.
Sunday
Take your time over breakfast before exploring more of Windsor, visiting LEGOLAND if you are travelling with children, or simply enjoying a slower walk around town.
And if you are visiting towards the end of October, you can build the Halloween walking tour or a Theatre Royal performance into the evening.
The advantage of staying for two or three nights is that you do not have to choose between everything.
There is a tendency to think of Windsor as somewhere you visit for the Castle and then leave.
October makes a good argument against that.
There are cultural events happening across the town, family activities during half term, evening entertainment, theatre, Halloween experiences and events that you probably would not associate with Windsor at first glance.
Add the Castle, the Long Walk, Eton, the Thames, restaurants and the town’s historic streets, and there is more than enough to fill a weekend.
So if you have been considering a Windsor short break, October is a good time to do it.
Pick an event. Find somewhere comfortable to stay. Leave enough room in the itinerary to explore without rushing.
And let the rest of the weekend take shape from there.
Explore Castle Properties‘ collection of serviced accommodation in Windsor and Eton and find a house or apartment that works for your group, whether you are visiting for a family half-term break, a theatre weekend, a Halloween trip or simply a few days away.
Make it a Windsor weekend → Explore our properties
