The Hawkesbury is one of Australia’s oldest colonial regions, where heritage buildings quietly tell stories of early settlement, hospitality and community spirit. The Hawkesbury Heritage Business and Building Trail is the perfect way to explore this remarkable area while supporting the local businesses that continue to bring these historic spaces to life.

From early colonial landmarks to contemporary enterprises, the Hawkesbury offers visitors a rich blend of history, culture, shopping, dining and wellness — all set within beautifully preserved architecture.

Whether you’re planning a day trip from Sydney or a leisurely weekend escape, we invite you to slow down, explore, and experience history in the here and now.

Here’s a list to get you started on the trail:

RICHMOND

The Book Attic Nestled in former historic stables, The Book Attic is a charming independent bookshop offering a diverse range of titles and genres. More than just a place to browse, it provides a memorable reading experience in a unique heritage setting, making it a must-visit for book lovers. Open seven days a week. 11 West Market Street, Richmond.

Lil Miss Collins Housed in a beautifully restored former bank, this newly opened Café blends Richmond’s financial history with contemporary design. The space retains many original features, enjoy your visit inside this striking heritage building or relax in the peaceful outdoor courtyard. 290-294 Windsor Street, Richmond.

Barrels and Ashes  Built in the 1800’s, this Georgian style building has been known by many names and boasts a rich and colourful history. Today it is a welcoming bar and restaurant, offering a cosy indoor fireplace and a sun-drenched courtyard. The perfect place to be surrounded by history while enjoying a cocktail or a memorable meal. 122 Windsor Street, Richmond

Richmond School of Arts A much-loved local landmark, the Richmond School of Arts has played a prominent role in local cultural life for generations. Dating back to 1861, it continues to serve as an important venue for events, performances, exhibitions and gatherings. 26 West Market Street, Richmond.

Richmond Regent Theatre The Richmond Regent is a charming reminder of the golden era of cinema. Its historic façade and continuing cultural role make it an essential stop on any Richmond heritage walk. Recently refurbished, it has reopened as a venue for concerts and movies. Click here to see what’s showing. 145 Windsor Street, Richmond

The Sunfire Kitchen Set inside a beautifully restored building from the 1860’s, The Sunfire Kitchen offers relaxed dining with a side of heritage charm. Perfectly positioned on Richmond’s main street, opposite Richmond Park, it’s an ideal final stop after a day of discovery. 179 Windsor Street, Richmond.

WINDSOR

Beauty at the Heritage – Old Windsor Post Office This sanctuary of beauty and wellness is in the former Windsor Post Office dating back to the early 1900’s. Enter this serene setting where you can relax and rejuvenate all while wrapped in history. 168 George Street, Windsor.

The Former Royal Picture Theatre Opened in 1926, this cultural landmark has had many lives and now it’s home to Wildbunch Florist and Antrim Homewares, both worth visiting for unique finds and a glimpse into history. 180 George Street Windsor.

The Church Bar, Windsor Dine inside a former church dating back to 1869.This unique space blends historic architecture with modern atmosphere, creating a memorable dining experience. Ideal for weekend breakfasts or cosy midweek meals. 22 Kable Street, Windsor.

89 Thai at Windsor Once a place for deposits and withdrawals, this red brick Georgian Revival building now serves delicious Thai cuisine. Formerly the Bank of New South Wales (later Westpac) it offers a setting rich in character and history. Located in the heart of Windsor, it’s the perfect stop for visitors exploring the town centre.146 George Street, Windsor.

Macquarie Arms Hotel, Windsor Established in 1815, the Macquarie Arms Hotel is Australia’s oldest continuously licensed pub. Enjoy a meal or drink in this nationally significant heritage building while soaking up over 200 years of history. Local tip: Be sure to head upstairs — there’s more to discover. 99 George Street, Windsor

The Reiki Nook & Gong Fu Tea Ceremony – Windsor Tea House Located in a heritage building, this tranquil venue offers wellness experiences and traditional tea ceremonies. It’s a peaceful stop that highlights how historic spaces can support modern wellbeing practices.  180 George Street, Windsor.

Beyond the Town Centres: discover Hawkesbury’s historic villages

Australiana Pioneer Village A living history attraction featuring historic buildings, exhibits and demonstrations that showcase early Australian life. It’s a family-friendly way to experience the Hawkesbury’s pioneering history. Open Sundays.  10 Rose Street, Wilberforce.

Ebenezer Church Australia’s oldest church, Ebenezer Church is one of the most significant heritage sites in the Hawkesbury. Experience a powerful connection to early settlement whilst exploring the pioneer-built church, the school-master’s house, the colonial graveyard all by the Hawkesbury River. Enjoy a Devonshire tea while you’re there. 95 Coromandel Road, Ebenezer.

Tizzana Winery Ebenezer Established in the late 1800s, Tizzana Winery offers a taste of Tuscany wrapped in rich history. The lovingly restored sandstone and timber building is National Trust–listed, preserving its original charm and character. Enjoy the full agritourism experience as you wander through the vineyard, sample locally crafted wines, and savour home-cooked meals. You can even stay overnight in the charming B&B accommodation for a complete countryside escape.  518 Tizzana Road, Ebenezer.

Bird in Hand Hotel, Pitt Town This heritage listed building dates back to the 1840’s and was restored in 1986. Now a popular local landmark in the middle of town it offers a warm welcome and hearty meals with a taste of Hawkesbury history. 81 Bathurst Street, Pitt Town.

Old Shed Distillery Once a sawmill, apple sorting facility and honey extraction site, this century-old building now operates as a distillery, producing handcrafted, small-batch spirits. It’s a perfect stop for something unique and local.  2419 Bells Line of Road, Bilpin.

Lochiel House Built in the early 1800’s and originally named Ivy Lodge, Lochiel House is the oldest structure in Kurrajong Heights. Now it offers a cosy setting with open fireplaces, a shaded courtyard and beautiful heritage interiors that blend history with modern comfort. 1259 Bells Line of Road, Kurrajong Heights.

Wisemans Inn Hotel and Cobham Hall Museum Commissioned by Solomon Wiseman and built in 1826 by convict labour, this hotel reflects 19^th Century architecture with sandstone walls and exposed rafters. Today it operates as a charming local pub with great food and a museum showcasing its fascinating past. Definitely worth a visit. 5545 Old Northern Road, Wisemans Ferry.

Settlers Arms Inn Step back into Australia’s colonial past in this heritage-listed Georgian-style inn built in the 1830s from convict-hewn sandstone. Rich in history and atmosphere, this iconic riverside inn invites visitors to linger over a meal and imagine the days when Cobb & Co stagecoaches once pulled up outside. 1 Wharf Street, St Albans.

For more heritage pubs, click here.

With so many places to explore along this historic trail, why not stay for a weekend? Click here for accommodation options.