Whether you’re drawn to the allure of ancient architecture, royal elegance, ghost tales or simply the quest to rest your bones after a day of sighteeing, having cocktails in Windsor can provide be a history lesson all on its own.

In no particular order, here’s a guide to five historic places in and around Windsor where you can soak in the history while sipping exceptional cocktails.

Great Fosters
Great Fosters version of the Champagne Cocktail features it’s own label gin, strawberry, lime and a champagne float.

1. The Shambles Bar

Address: 51 High Street, Windsor SL4 1LR

The Crooked House is one of the town’s most charming and recognizable landmarks. Its peculiar architecture and rich history make it a must-see for visitors exploring Windsor’s storied past.

The Crooked House was originally constructed in 1592 as a market house. These were common features in English towns where traders could sell their goods. Situated on the High Street, its location made it a focal point for commerce and community gatherings in Windsor. The building’s timber-framed design was typical of the period, showcasing the traditional construction methods of the time.

Currently owners Pip and Hamish have transformed the crooked house into a wine bar with the recent addition of craft cocktails. Despite its tourist-y location, it’s become a favorite place for cocktails in Windsor among locals. It makes our list of Best Spots for Coffee in Windsor, but they are best known for their wine and cocktail selection.


2. Incognito

Address: 13a High Street, Windsor SL4 1AD
Hours: Wednesday-Sunday: 5:00 PM – 11:00 PM

The bar’s entrance is deliberately discreet. There is no overt signage, so you’ll have to seek out this hidden treasure. Incognito captures the spirit of the Prohibition era with its secretive and sophisticated ambiance.

The building has a storied past, with its origins tracing back to the 18th century. Originally, this site was part of the bustling market district and served various functions, including a stint as a gentlemen’s club in the 1800s. Its clandestine allure made it a fitting home for a speakeasy-style bar.

Each cocktail is designed not only to tantalize the taste buds but also to provide a sensory experience, making every visit to Incognito Bar memorable.

Incognito Bar Windsor
The door to Incognito is unmarked and you’ll ring the bell to gain entrance to this speak easy feeling cocktail bar.

3. Number 19, Eton

Address: 19 High Street, Eton SL4 6AX
Hours: Thursday-Sunday: 4:00 PM – 12:00 AM

Nestled in the historic town of Eton, Number 19 is considered a hidden gem by locals. A barber shop by day, owners Gail and Michael magically transform the space into an atmospheric wine bar. 

You can have a cocktail, but why not sample British Fizz? Ordered alongside a carefully curated cheese plate, the combination makes for an elegant evening.

Locals tip: Hours can vary and tables can be scarce, so best to call to confirm hours and book a table ahead


4. The Cobbles

Address: 8 Market Street, Windsor SL4 1PB
Hours: Monday-Saturday: 12:00 PM – 11:00 PM; Sunday: 12:00 PM – 10:00 PM

The Cobbles is housed in a historic coaching inn from the 17th century. It originally served travelers and their horses along the bustling trade routes into Windsor. The cobblestone entrance and rustic interior reflect its rich heritage.

Don’t miss the “Coachman’s Cup,” a robust mix of whiskey, ginger ale, and aromatic bitters, which pays homage to the inn’s equestrian past.

This venue’s quaint charm caught the eye of filmmakers, making it a backdrop for scenes in the movie “The Other Boleyn Girl” (2008).


5. Great Fosters

Address: Stroude Road, Egham TW20 9UR
Hours: Monday-Sunday: 12:00 PM – 10:00 PM

Set within a Grade I listed mansion, Great Fosters offers an opulent experience with its Elizabethan architecture and lush gardens. Built in the late 1500s, the mansion has been meticulously preserved and now serves as a luxury hotel and cocktail bar. It was used as a hunting lodge for Henry VIII and Queen Elizabeth 1, and the “Mad King George” escaped here for periods of recovery. It makes our list of top spots for Afternoon Tea in and around Windsor, but also provides an elegant atmosphere for drinks.

The bar is well stocked, but a cocktail made with Great Fosters own gin is an experience that can’t be had anywhere else. There couldn’t be anywhere more beautiful than a G&T on their beautiful terrace overlooking the gardens.

Great Fosters is a short drive from Windsor and provides an elegant backdrop for cocktails.

6. The Two Brewers

Address: 34 Park Street, Windsor, SL4 1LB
Hours: Monday-Thursday: 11:00 AM – 11:00 PM; Friday-Saturday: 11:00 AM – 11:30 PM; Sunday: 12:00 PM – 10:30 PM

Nestled at the end of a picturesque street that leads directly to Windsor Castle’s Long Walk, The Two Brewers is a historic pub that has been a cornerstone of Windsor’s social and cultural life for over two centuries. Established in 1792, this is a classic atmospheric English pub with candles in the windows, roaring fires in the fireplaces, low beamed ceilings, packed gallery walls and bookcases.

The location at the end of Park Street makes it an ideal place to cap a trek on the Long Walk.

The pub offers beer from local breweries, a selection of wines and spirits. Outdoor tables provide a charming open air space. It’s an ideal spot for enjoying a tipple in warmer weather.

Locals tip: Two Brewers does not serve shots, presumably to curtail drunkenness. If you feel you must, a loophole is to order your spirits “Neat”. The Two Brewers is popular with both tourists and locals and getting a table can be a challenge. Book a table to avoid disappointment, but doing so requires a food order in addition to drinks.

7. All Bar One Windsor

Address: 40A Windsor Royal Station, Windsor, SL4 1PJ
Hours: Monday-Thursday: 10:00 AM – 11:00 PM; Friday-Saturday: 10:00 AM – 12:00 AM; Sunday: 10:00 AM – 10:00 PM

If your goal is “One of the Road”, All Bar One is adjacent to the platform at Windsor Eton Central Station. Yes, it’s a chain, and once inside it looks like the others. It’s the location that creates a rich historical backdrop.

Windsor Royal Station itself was built in 1849 as the end of the District Line, but its location made train travel to and from Windsor Castle possible for Queen Victoria. Prince Albert influenced the station design.  All Bar One is housed in what was originally a “Waiting room” for her majesty. Adjacent to All Bar One is a replica of the Royal Train.

Conclusion

Whether you’re a history buff, a cocktail enthusiast, or someone looking to explore the quaint charm of Windsor, these bars provide an enchanting journey through time, enhanced by their remarkable cocktails. Enjoy your drink, and let the stories of the past enrich your experience!