The North Star, Maidenhead

My first stop today was at The North Star, a friendly, traditional back-street pub in Boyn Hill. It has two bars: a busier public bar with TV & darts, and a quieter lounge.

It is registered as an Asset of Community Value (ACV). They host quiz nights (every other Thursday), occasional live music, and support darts & cribbage. A small front patio offers outdoor seating; the pub is dog friendly.

The North Star is well regarded for its atmosphere, friendliness, and being a genuine local.

A walk then took us to our next venue:

The Craufurd Arms

This pub is Maidenhead’s first community-owned pub (since purchase in 2017), run for and by locals. It stands on Gringer Hill, a short walk from the centre.

They serve four local real ales at present – one from Stardust and three from Rebellion. The pub has earned a Good Beer Guide entry for 2026.

Inside, there is a cosy single bar, and they have a partially covered beer garden. They host frequent community events: quiz night, live music, open mic, darts, etc.

The pub’s name (unusually spelled “Craufurd”) comes from its historical link with a nearby private school (Craufurd College).

We then walked back towards the centre of town to:

The Maiden’s Head

A long-standing town centre pub & eatery on Maidenhead’s High Street. They emphasise local real ales (from breweries such as Rebellion, Windsor & Eaton, Vale, Hardline) alongside a wide beer, cider and zero-alcohol range.

It positions itself as more than just a pub: a community focal point and a “pub & eatery” with live music at weekends.

From there it was a very short walk to:

The Bear, Maidenhead

The Bear in Maidenhead is one of the town’s oldest named inns, with records dating back to 1489, when its landlord was fined for “an unlawful price for provisions.” The original Bear stood at the corner of Park Street and High Street, serving as a central meeting and lodging spot for locals and travellers alike. Its long-standing name and reputation made it a fixture of Maidenhead life for centuries.

During the 19th century, The Bear became a prominent coaching inn, catering to passengers on horse-drawn routes between London and the West Country. In 1845, the establishment moved to new premises at 8–10 High Street, the site it still occupies today. This building, with its distinctive 19th-century façade, has since earned Grade II listed status, recognising its historical and architectural importance within Maidenhead’s evolving town centre.

Today, The Bear is operated by J D Wetherspoon, which reopened the pub under its brand in 2010. A major £665,000 refurbishment in 2024 modernised its interiors while retaining its period character, ensuring it remains a valued community hub. With its mix of deep-rooted history and modern hospitality, The Bear continues to represent both the heritage and the ongoing vibrancy of Maidenhead’s High Street.

The next stop was a little East from the centre:

The Lord Grenfell, Maidenhead

The pub now known as the Lord Grenfell in Maidenhead traces its origins back to an earlier incarnation called the Grenfell Arms, located on Oldfield Road in Maidenhead, Berkshire. At one point it was re-named the Guardsman Inn when the landlord chose to dedicate the venue to the local Guards regiments and refurbished it with memorabilia. In 2013, the pub reverted to its former “Grenfell Arms” name under new licensees who wished to honour the local heritage and the legacy of William Grenfell, 1st Baron Desborough, the long-time High Steward of Maidenhead.

In recent years the pub underwent a significant transformation and was re-branded as the Lord Grenfell, repositioned as an ale-and-cider house with cask ales, craft keg lines and even eight bedrooms upstairs. By late 2024 it was recognised for its community focus and quality beer offering, winning the local CAMRA “Pub of the Season” award.

Thus, the story of the Lord Grenfell is one of evolution from a traditional local pub in Maidenhead, through a themed iteration honoring the Guards, back to a refreshed modern pub and lodging venue that blends craft beer culture, local heritage and accommodation.

From there we headed back to the centre:

A Hoppy Place, Maidenhead

This is a relatively new but ambitious craft-beer bar / micropub / bottleshop operating in Trinity Place, Park Street, Maidenhead.

It opened in 2022, featuring 4 cask lines, a number of keg lines, and a vast selection of bottled and canned beers in the fridges.

It has an excellent selection and warm welcome with friendly and knowledgeable staff, lots of beer variety and a relaxed, beer-lover’s atmosphere.