Housed in a heritage sandstone cottage, Eschalot is emblematic of the Southern Highlands’ dining scene. Here, chef Matty Roberts sources much of the produce from the restaurant’s own gardens. You’ll likely see chefs carrying leafy radishes or sun-sweetened tomatoes heading straight into service. Opt for the chef’s ‘feed me’ menu to enjoy those just-harvested ingredients in dishes such as eggplant crisps, burrata and local honey. 24 Old Hume Hwy, Berrima; eschalot.com.au

Begin your journey at Bendooley Estate by browsing in its Book Barn, a reimagined rural shed stacked with old and new titles. Flick through a few cookbooks, such as the fab SALATA. by Michael Rantissi and Kristy Frawley, for a little inspiration before lunch. Then settle in around a sun-lit table at the Book Barn Restaurant to best enjoy Berrima’s bounty. 3020 Old Hume Hwy, Berrima; bendooleyestate.com.au/dining

A hangout for members drawn from Berrima’s various tribes, this all-day spot keeps things simple and low-key. Sip on a perfect little piccolo while tucking into a croissant made sticky with jam from the 1910 Bottling Company’s organic fruit preserves. Bring an eco bag to stock up on fresh, local produce and artisan ingredients. 1/13 Old Hume Hwy, Berrima; @generalstorecafeberrima

Gumnut Pâtisserie helped put Bowral on the map as one of the best regional towns in Australia for eating and drinking. The pâtisserie, led by pastry chefs Tracy and Vicki Nickl, also has a loyal following at its sister venues in Berrima and Mittagong. Expect meticulously crafted pastries, pies and desserts made with top-tier ingredients and zero shortcuts. A must-stop when visiting Berrima. 1 Old Hume Hwy, Berrima; gumnutpatisserie.com.au

Josh’s Café is a Berrima institution. If there’s a choice of seating, opt for a table in the courtyard, which looks like something out of a fairy tale at night. As well as keeping the customers entertained, chef Joshua Levings keeps the kitchen on an even keel cooking up modern Middle Eastern food with Turkish accents. Check the blackboard to get a taste for what’s in season at this local favourite. 9 Old Hume Hwy, Berrima; @joshscafeberrima

Wear something fabulously floofy to high tea at this award-winning cupcake store and tea house, wreathed in flowers and pops of pink. Freshly baked cupcakes and scones take centre stage here during high tea served in a space that knows its audience (tween birthday parties, mothers and daughters). Use your dad’s burner phone to sidestep the U16s social media ban and snap some selfies for your socials. Shop 2/30 Old Hume Hwy, Berrima; thecupcakeco.com.au

After lunch at the Book Barn, move through to the architecturally designed Cellar Door to sample the estate’s wines or return after dark for Leo’s by Night. The fine dining experience is inspired by the estate’s late patriarch Leo Berkelouw and his love of literature, food, and wine. The space brings these passions together for a magical wining and dining experience. 3020 Old Hume Hwy, Berrima; bendooleyestate.com.au/dining

A visit to Tractorless Vineyard begins with a tour explaining the regenerative practices in play such as the deployment of sheep to mow the lawn and fertilise the vineyard. From there, it’s into the rustic shed to taste wines shaped by minimal intervention. The focus at the vineyard is all about bringing the soil back to life and tasting wines that have a clear sense of place. 132 Compton Park Rd, Berrima; tractorlessvineyard.com.au

The Southern Highlands is making a name for itself as a cool-climate wine region. Sip your way through the bucolic landscapes of the region on the Wine Trail before popping into the PepperGreen Estate Tasting Room in the centre of Berrima. Snag a sample of the award-winning 2024 Semi Dry Riesling Single Vineyard which won gold at the 2026 Sakura Japan Women’s Wine Awards before enjoying a long lunch curated by head chef Mark Chance. 13 Market Pl, Berrima; peppergreenestate.com.au

New cafes and restaurants have been popping up all over the Southern Highlands in recent years. But the Surveyor General Inn has stood the test of time, dating back to 1834. The list of tap beers at the Surveyor General Inn is extensive and there’s often live music. But it’s the pub grub that draws local patrons: think hot wings with blue cheese mayo, pork belly burgers or tacos with guacamole and tangy tomato salsa. 26 Old Hume Hwy, Berrima; surveyorgeneralinn.com.au

Stay onsite at Bendooley Estate in studio retreats or two- and three-bedroom cottages dotted across the grounds. Interiors are thoughtfully detailed with inviting living spaces and wide outlooks over the lake, valleys and manicured gardens. Mornings start with wisps of mist lifting off the water; evenings end with a short walk back from Leo’s By Night for a bath and a good book. 3020 Old Hume Hwy, Berrima; bendooleyestate.com.au

It’s only a short drive to Bowral from Berrima where this country manor is the ideal spot to stay in the Southern Highlands. The hotel features landscaped grounds, two tennis courts, a heated indoor pool and generous rooms with queen-sized beds to collapse into afterwards. Stay an extra few nights in the Southern Highlands so you can enjoy dinner by the fire at the Bistro Sociale dining room. 6 David St, Bowral; beridahotel.com.au

Dress in your Bridgerton best to join Berrima Walking Tours for a few hot laps of the Southern Highlands village. That connection with Berrima’s colonial past continues with a stay at Peppers Craigieburn where the heritage of the original homestead is carried through at the estate, which dates back to 1887. We’re talking wide verandahs, established gardens and classic interiors with enough space to stretch out between long walks around the grounds. Centennial Rd, Bowral; peppers.com.au

Oldbury Cottage is one of the most romantic places to stay in Berrima, a heritage-listed one-bedroom escape for two. The restored 1850s cottage pairs original rustic timbers with contemporary comforts, including a fireplace and terrace. Pick up provisions from Little Piggy Deli and a bottle of plonk from Bendooley Estate and retreat fireside for a cosy Southern Highlands stay. 7 Oldbury St, Berrima; oldburycottage.com.au

Bounce around the Southern Highlands by day checking off local attractions like Berrima District Museum, Whitewall Art Projects and Berrima Courthouse. Come evening, check into Links House in nearby Bowral, a boutique stay with just 17 rooms overlooking the golf course. Stroll around the leafy gardens, enjoy dinner at Ethos restaurant and consider this well-placed property as the perfect base from which to explore the Southern Highlands. 17 Links Rd, Bowral; linkshouse.com.au