Weekend in Windsor, UK | Travel Guide and 2-Day Itinerary

by Jon Miksis
Weekend itinerary in Windsor, UK
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What a weekend in Windsor UK looks like:

As you’ll discover in this travel guide, there are so many interesting and unique things to do during a weekend in Windsor, UK.

As we stepped off the train in Windsor, we were greeted with a light breeze and drizzle — a proper welcome to the English countryside.

Once we exited the train station, we were immediately drawn to the colossal castle looming overhead. We had expected Windsor Castle to be large and luxurious, but we were awestruck by its sheer stature in the heart of town.

As we set foot in this quaint community for the first time, we were enchanted by its timeless intrigue. Based on my weekend in Windsor, I’ve put together an itinerary and travel guide to help you maximize your time in England’s royal retreat.

Weekend in Windsor pinterest image.

Windsor, the Queen’s royal residence

Queen Elizabeth II, the world’s longest reigning monarch, spends many of her weekends in Windsor. For the 92-year-old Queen, Windsor Castle provides a royal retreat from the hustle and bustle of London.

Every year during the March-April timeframe, Queen Elizabeth assumes her official “Easter Court” duties at the castle, where she hosts state events for politicians and public figures.

Every June, the Queen spends a week in Windsor to attend the Order of the Garter and Royal Ascot events. The Order of the Garter is a ceremony in which the Queen recognizes and appoints knights for their distinguished public service. The Royal Ascot is a 5-day horse racing meet that hosts over 300,000 guests. The most distinguished guest is undoubtedly Her Majesty, who makes a royal entrance in a horse-drawn carriage.

From holding and attending events to enjoying the serenity of her 13-acre property, Queen Elizabeth considers Windsor her home.

Windsor Castle's Cambridge Gate, a weekend itinerary and travel guide in Windsor in 2020.
Cambridge Gate at Windsor Castle.

Getting to Windsor

Windsor is conveniently located less than 30 miles from London and 10 miles from London Heathrow Airport. As such, Windsor is most accessible by taking a train or renting a car. If you opt to take a train directly from London, I recommend riding via South Western Railway to the Windsor & Eton Riverside Station. The following stations in London do not require any transfers to Windsor:

  • Vauxhall Rail Station, London (12 stops; 50 minutes)
  • Waterloo Station, London (13 stops; 54 minutes)

At the time of my trip, one ticket cost $15 each way. You can either purchase your tickets online in advance, or at a ticket kiosk in the train station.

Getting around Windsor

As a small town with only 32,000 residents, Windsor is easy to cover on foot. Most top sights in Windsor and the neighboring town, Eton, are within a 15-minute walking distance. If you plan to do any excursions outside of these twin towns, consider taking a bus or taxi.

For an updated bus schedule, I recommend stopping by the Royal Windsor Information Centre inside the Windsor Royal Shopping Mall. This information center is open seven days a week, providing visitors with advice about Windsor and the surrounding communities. Additionally, you can purchase discounted tickets for local attractions and events.

If you’d like to take a taxi, make sure to give yourself ample time to find one. Based on my experience, there is a short supply of them patrolling Windsor (as is often the case with small towns). Rather than walking around looking for one, I recommend waiting at the taxi stand next to Windsor Castle, at the intersection of Peascod Street and High Street.

If you anticipate doing multiple day trips to the surrounding towns, renting a car is probably your best option.

Windsor, a town steeped in history

The town of Windsor was established during the 11th century under the reign of William the Conqueror. It was here where he decided to build Windsor Castle, a fortress and royal residence just south of the River Thames. This location was ideal because of its proximity to London and the surrounding woodlands for hunting.

During subsequent monarchs, Windsor Castle became more of a royal palace than a fortress. The original timber fortifications were replaced with stone, and royal apartments were added to the castle complex. In the 14th century, St. George’s Chapel was built inside the castle walls, becoming a site of royal ceremonies, weddings, and burials.

As Windsor’s royal presence burgeoned, so did the demand for merchants and workers. By the end of the Middle Ages, Windsor was one of the wealthiest towns in England. Medieval homes and storefronts were erected during this time, some of which are still standing to this day.

Windsor was so historically prominent that Windsor, Ontario—the southernmost city in Canada—was named after it.

To grab a front-row seat of Windsor’s rich heritage, it’s worth finding an accommodation in a central location.

River Thames and Windsor Castle, weekend itinerary and travel guide
The Eton side of the River Thames offers a unique perspective of Windsor Castle. It’s a must-see during a weekend in Windsor in 2020.

Where to stay in Windsor

Known as London’s Country Estate, Windsor is the perfect place to stay and explore southern England. Windsor’s close proximity to London, and the towns of Ascot, Bray, and Cookham, make it a convenient alternative to staying in the city.

When visiting historic places in Europe, it always pays to stay in the heart of the old town. The Sir Christopher Wren Hotel and Spa is at the center of all the action in downtown Windsor. This 4-star property is a complex of historic buildings that straddles the River Thames. The Sir Christopher Wren Hotel is situated on a charming cobblestone street, only a 2-minute walk from Windsor Castle.

In addition to its historic elements, the Sir Christopher Wren Hotel also has many modern amenities, including a conference center, jacuzzi, and sauna. In the morning, The Brasserie offers a hearty English breakfast. This traditional breakfast includes Eggs Benedict, fresh tomatoes, baked beans, and toast, among an assortment of fruits, vegetables, and breads. Beyond the delicious meals, my favorite part about The Brasserie was its idyllic riverside setting. Be sure to get to the breakfast buffet early to snatch a window seat!

Among the 50 hotel properties in Windsor, the Sir Christopher Wren Hotel and Spa is one of the best valued. Double rooms start from £130.00 per night. Its location alone is a big draw, and the vibrant rooms and modern amenities are a bonus.

If you book directly through the hotel website, you’ll get a free drink at The Brasserie.

Sir Christopher Wren Hotel and Spa
Sir Christopher Wren Hotel and Spa

How to spend your first day in Windsor

Below, I’ve highlighted some of the top sights and attractions you’ll want to see on day 1 in Windsor. In addition to this itinerary, refer to the “Day trips, outings, and excursions” section later in this article for more inspiration on things to do during your weekend in Windsor.

Watch the Windsor Castle Guard Change

To start your weekend on the right foot, march up the hill to Windsor Castle to watch the Guard Change. This royal ritual begins at 11am on Saturdays, but I recommend arriving at 10:45am to grab a spot at the intersection between Peascod Street and High Street. During this spirited ceremony, you’ll catch a glimpse of royal guards marching up to Windsor Castle, escorted by a chivalrous musical ensemble.

As of January 2020, the Windsor Castle Guard Change occurs every Tuesday, Thursday, and Saturday at 11am. This schedule is subject to change, so be sure to check the official website to see the updated times of these ceremonies.

Guard Change, weekend itinerary and travel guide in Windsor, UK
The Guard Change is a fun and lively public spectacle. The guards march right through the center of town, from Victoria Barracks to Windsor Castle.

Grab a bite to eat and go shopping on Peascod Street

After the Guard Change, head down Peascod Street for an early lunch or to go shopping. This pedestrian street is home to an array of restaurants, cafés, independent shops, and high-end retailers. Peascod Street is also lined with street food stands, serving everything from pastries to paella.

As you stroll down Peascod Street, be sure to turn around periodically to view the epic backdrop of Windsor Castle. This iconic structure is definitely one of the most Instagrammable places in the UK.

Peascod Street in Windsor
Windsor Castle towers over Peascod Street.

Other sights you’ll inevitably stumble upon

As you head further down the road and away from the castle, Peascod Street will eventually become St. Leonards Road. This is where you’ll find some of the most authentic and inexpensive shops in town.

If you’re not sold on the culinary options you’ve seen so far, head back towards the castle and take a left into the Windsor Royal Station. This railway-station-turned-shopping-center is now home to a motley collection of 40 shops, including restaurants and boutiques. The Windsor Royal Station was built in the 1850s, and its Victorian-style elements are still visible inside the mall today.

While you’re having a bite to eat, you can explore some of the following options for the remainder of the afternoon.

Windsor Royal Station, weekend itinerary and travel guide
Windsor Royal Station provides a unique shopping experience that will likely be a part of your weekend itinerary.

Take a riverboat cruise along the Thames (seasonal)

As you’re digesting your hearty English lunch, consider taking a short cruise on the River Thames. There are several boat cruises that offer breathtaking views of Windsor, Eton, and the scenic sights within them. Some landmarks that you’ll see along the way include the Windsor Castle, Royal Windsor Racecourse, and Eton College Chapel.

There also some lunch and dinner cruises that explore places further downstream; some going as far as London. I recommend checking TripAdvisor to find a riverboat cruise that best aligns with your preferences!

River Thames and Windsor
Some cruises on the River Thames are seasonal, running from April through October. This is a must-do during a weekend in Windsor in 2020.

Stroll through the Alexandra Gardens

The riverboat cruise will drop you off along the Windsor Promenade, which is next to the Alexandra Gardens. This pretty park is perfect for picnics, bike riding, and simply enjoying the outdoors. For families with children, there is a mini-amusement park with a few different rides. Also, there are plenty of seating areas with stunning views of Windsor Castle.

Jubilee Fountain in the Alexandra Gardens
The Jubilee Fountain springs to life at night with luminescent colors – a must-see during your weekend itinerary in Windsor.

Explore Windsor’s twin town, Eton

Definitely add this to your Windsor UK itinerary.

From Windsor, cross over the Eton Bridge, and you’ll find yourself in the neighboring town of Eton. With a population of only 4,700, this historic town is much smaller than Windsor.

As you begin your trek down the Eton Walkway, you’ll encounter an eclectic mix of restaurants, cafés, and shops. Eton is most famous for its prestigious high school, Eton College (in the UK, “college” refers to “high school”).

Eton College is an all-boys boarding school that was founded by King Henry VI in 1440. Since then, Eton College has held a distinguished student body—including 19 prime ministers and members of the royal family. Both Prince William and Prince Harry attended Eton College.

Within the school grounds, you’ll come across the Eton College Chapel. Built in the 15th century, this chapel was designed in the late Gothic style. As you stand beside the Eton College Chapel, you’ll be amazed by its sheer size and stature.

Eton College Chapel, weekend itinerary and travel guide in Windsor
Eton College Chapel

Museums in Eton

If you’re fond of history museums, consider checking out the Eton College Natural History Museum and Museum of Eton Life. These museums underscore the school’s dedication to the arts, sciences, and student life. They are officially opened on Sunday afternoons from 2:30-5pm; however, it’s possible to arrange a visit outside of their standard hours by contacting the Museum Officer. If you don’t wish to go inside, I recommend walking around the periphery of the school and museums to admire their magnificent architecture.

After feeding your hunger of history, you’ll probably want to satisfy another craving—sweets. On your way back to Windsor, pay a visit to the Eton Fudge Shop, located just across the bridge from Windsor, for some traditional English fudge. Be sure to save some room for dinner, though.

Eton Bridge, weekend itinerary and travel guide in Windsor
The historic town of Eton is a top sight that you can’t miss during your weekend itinerary in Windsor.

Relax on a park bench or stroll around Windsor before dinner

As afternoon becomes night, consider relaxing on a bench along the River Thames as you decide on your dinner plans. On a warm summer night, in particular, this is among the top things to do during a romantic weekend in Windsor. The Windsor Promenade and Eton Bridge offer scenic views of the river and Windsor Castle. Each is a great vantage point for catching the sunset as well.

If you decide to head back into Windsor, you’ll surely find yourself in one of its delightful cafés or restaurants. Later in this article, I’ve highlighted a few dining options that offer a taste of Windsor’s food scene.

As you wrap up your first day in Windsor, perhaps with a local ale in hand, be prepared to hit the ground running on day 2.

Top sights to explore during your second day in Windsor

Begin your day by getting breakfast somewhere along the River Thames or near Windsor Castle. From there, you’ll want to arrive at the castle by 10am to begin your tour inside.

Experience 900 years of royal history inside Windsor Castle

This is a must during a weekend in Windsor, UK.

To avoid long lines, I recommend getting to Windsor Castle right when it opens at 10am. Purchasing your tickets in advance is advisable, particularly if you’re visiting during peak season.

Windsor Castle Quadrangle, weekend itinerary and travel guide
The Quadrangle is a courtyard inside the castle that connects the Queen’s residence with the State Apartments. Windsor Castle is the highlight of your weekend itinerary.

Once you step inside the castle walls, you’ll quickly realize its sheer size. Founded in the 11th century, Windsor Castle is the largest and oldest occupied castle in the world. There is so much intriguing history behind this castle, so be sure to grab a free audio guide at the entrance to accompany you during your stroll. I recommend allotting yourself 2-3 hours to explore the castle, its ramparts, and the chapel inside.

The audio tour will guide you through the castle courtyards and into the State and Semi-State Apartments. These lavish rooms are brimming with fine artwork, gilded murals, and royal relics. The ornate furniture and paintings make you feel like you’re back in medieval times. Prince Harry and Meghan Markle’s wedding outfits were on temporary display here last year.

St. George’s Chapel is another obligatory stop

St. George’s Chapel is another must-see inside the castle. This 15th century Gothic church is where the Duke and Duchess of Sussex recently got married. It’s also a burial place for 10 monarchs, including Henry VIII and Charles I.

St. George’s Chapel is open daily except for Sundays; however, you can attend the church services that take place at 10:45am, 12:00pm, and 5:15pm. Refer to the St. George’s Chapel website for their official visiting hours.

After completing your tour of the castle and the photo opportunities that come with it, it’s time for lunch. Given that daylight is limited, consider grabbing a quick bite to eat at one of the street food vendors on Peascod Street, a café, or a fast-casual restaurant like Pizza Express. Then, head over Windsor Great Park to stroll its iconic tree-lined path.

St. George's Chapel inside Windsor Castle, weekend itinerary and travel guide
St. George’s Chapel is a “Royal Peculiar”, meaning that it’s under the jurisdiction of the Monarch rather than the Church of England. As part of your weekend itinerary in Windsor, be sure to go inside or attend a church service.

Take a walk in the Windsor Great Park

Just south of Windsor Castle, you’ll come across a pretty tree-lined avenue called The Long Walk. Consistent with its name, The Long Walk is quite a trek—extending 2.6 miles from the Windsor Castle Gate to the Copper Horse Statue of King George III. During your Sunday stroll, you may be lucky enough to spot some wild red deer, which often prance through the park.

Once you arrive at the copper horse statue on Snow Hill, you will be at the highest point in Windsor Great Park, where you’ll enjoy spectacular views of Windsor Castle.

During your trudge through the Windsor Great Park, you’ll be dazzled by its seemingly endless paths and trees. The park is 4,800 acres and contains everything from historic monuments to ancient oak trees. Just to put its size in perspective, Central Park in NYC is 843 acres and Hyde Park in London is 350 acres.

The Long Walk, weekend itinerary and travel guide in Windsor
The Long Walk is a scenic stroll with impeccable views of Windsor Castle.

Reflect on your weekend in Windsor as you walk along the Queen’s Walkway

To wrap up your last day in Windsor, follow the Queen’s Walkway to re-visit some of your favorite sights in town. This pavement path links together 63 of Windsor’s top attractions and parks. The Queen’s Walkway was dedicated to Queen Elizabeth II in 2015, in honor of her becoming the longest reigning monarch in history.

As you stroll through Windsor one last time before sundown, you’ll be walking in the steps of monarchs from centuries past who called this treasured town their home.

Queen's Walkway, weekend itinerary and travel guide in Windsor
The Queen’s Walkway is a quintessential part of your weekend itinerary in Windsor.

Day trips, outings, and excursions

Windsor is a great home base for exploring London and the surrounding areas. There are plenty of exciting day trips and excursions within close proximity of Windsor, and I’ve highlighted some of the top ones below.

Ascot Racecourse

Horse racing has been a part of British culture for centuries. The Ascot Racecourse, founded in 1711 by Queen Anne, is one of the most popular horse racing venues in the UK. Here, you can witness these competitive races firsthand alongside thousands of passionate (code word for “loud”) fans. Horse race betting is a £4.5 billion industry in the UK, so you can imagine the intensity and liveliness that lingers in the air at these races.

Horse racing in the UK isn’t just a sport, it’s also a fun social occasion. At the Ascot Racecourse, there is a wide selection of food, including lunch and afternoon tea with Champagne. The races themselves only last a few minutes at a time, and there is plenty of time to mingle in between.

Watching a race at Ascot

Ascot only hosts 26 days of horse races during the year, so be sure to book your tickets in advance. The most popular among these races is the Royal Ascot, which takes place from June 18-22 this year. Horse races tend to last over 3 hours, so be sure to plan your weekend itinerary in Windsor accordingly!

Just 6 miles from Windsor, the Ascot Racecourse is an idyllic countryside setting that makes for a local, authentic experience. Enjoy an ale, dress up in formal attire, and you’ll feel like you’re a part of this timeless horse racing tradition!

Ascot Racecourse Parade Ring, weekend itinerary and travel guide in Windsor
A weekend itinerary in Windsor would not be complete without a trip to the Ascot Racecourse. The Parade Ring (shown above) is where the horses and riders warm up prior to racing. It provides fans and bookies with a chance to see the horses before the race begins.

Legoland Windsor Resort

If you’re planning to bring children along on this royal retreat, you’ll probably want to carve out some time for the Legoland Windsor Resort. This lego-themed park is every kid’s dream, hosting an array of fun rides, shows, and building workshops.

Legoland is predominantly geared towards children ages 3-12, however, there is plenty to do for the whole family. According to the Legoland website, it’s advisable to book tickets at least 7 days in advance for the best deals.

Windsor Castle, Bath, and Stonehenge Tours from London

If you’d like combine London, Bath, and Stonehenge with your trip to Windsor, there are several tour companies that offer 6-10 hour tours from London. I recommend using TripAdvisor to find the right itinerary for you.

An organized tour is definitely something to consider if you’re strapped for time and would like to gain a high-level overview of these UNESCO Sites. I tend to prefer doing these excursions on my own, but a day trip tour is a great hassle-free option.

Where to eat in Windsor

Windsor’s rich cuisine perfectly complements its rich history. From casual eateries and street food to top-notch dining, Windsor is a haven for foodies. Below are a few dining options that mesh nicely with the local culture.

Bel and The Dragon

Bel and The Dragon is a historic restaurant in the heart of Windsor that has served hungry patrons since the 11th century. Their menu was devised by Chef Ronnie Kimbugwe, who was previously a Sous Chef of Gordon Ramsay.

Bel and The Dragon specializes in modern British cuisine, serving everything from poached duck egg and game stew, to smoked salmon and lamb shoulder. This restaurant also serves brunch on Saturdays, as well as afternoon tea and grub throughout the week. Bel and The Dragon has a rustic and relaxing ambiance that creates a cozy dining experience.

Located between Windsor Castle and Eton, Bel and The Dragon is an excellent dining option that should be on your weekend itinerary.

Windsor & Eton Brewery

The Windsor & Eton Brewery is a popular craft brewery located next to the Alexandra Gardens. Established in 2010, this brewery’s slogan is “making beer the biggest attraction in Windsor”. Its assortment of craft beers is every beer lovers dream.

Though this brewhouse doesn’t serve meals, they do have chips and nuts to accompany their beers. The Windsor & Eton Brewery also offers brewery tours that shed light on their brewing process. It’s open every day of the week except for Sunday.

Waterman’s Arms

Waterman’s Arms is a quaint, 17th century pub in Eton that serves local English beer and fine wines. This traditional restaurant only has nine tables, giving it an intimate, Old World vibe. It’s conveniently situated just across the bridge from Windsor and is one of the best hidden gems in the area.

A weekend in Windsor is simply not enough

From its rich history and scenic setting, to its fine dining and shopping, Windsor has so much to offer year-round.

Thinking of visiting Windsor during a weekend in 2020? I hope this weekend itinerary and travel guide of Windsor serves you well in exploring England’s royal retreat.

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*My trip to Windsor was in partnership with the Royal Borough of Windsor and Maidenhead and its affiliated partners. As always, all opinions are my own.



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