The new steakhouse in town. Great filets, dry-aged cuts and A5 Wagyu. Drinks are pretty fantastic too. Been a couple of times and it does not disappoint. Not cheap, but what is these days?
Over 50 wines you can self-serve from their wine dispensing machines. Get anything from a taste to a glass. Very fun. And if you get a little hungry, just order some food at the bar right there or head upstairs to their Rooftop restaurant (and try their fabulous salmon pizza with caviar!).
www.thematheson.com
Iggy’s and Angela’s is a relatively new burger and ice cream joint in town. Owned by mother and son duo, Iggy and Angela’s quickly became a town favorite for casual burgers, loaded fries, and topping it off with Angela’s ice cream (our favorites are Caramel Crack, Grasshopper, and Dulce de Leche brownie).
https://www.iggysburger.com/
https://www.angelasicecream.co...
New restaurant/specialty cocktail place from the people who used to work at Dukes. The "Almost Famous Chicken Tenders" are great.
www.loandbeholdca.com
Troubadour is a great sandwich shop during the day but now they provide a world-class French pop-up dinner in the same space. Be forewarned, you are sitting in a sandwich shop on stools and will pay $125/pp before wine (so not cheap), but the food is outstanding and the dishes (oh the dishes).
www.troubadourhbg.com
Fantastic and affordable Italian. Located in Windsor, just one town below Healdsburg. Large portions, good food, a relaxed, comfortable atmosphere and very affordable for restaurants around here. Not fancy but solid.
www.gratawindsor.com
Great, family-owned Itailan right in town. A great vibe and really good food. They also have a great wine room for groups.
www.bacicafeandwinebar.com
Small plate classic right in Healdsburg. Fantastic raw bar, great fish tacos and impressive lobster rolls. Many other options (even non-fish) as well. Great indoor and outdoor seating. A fun place.
www.starkrestaurants.com/stark-restaurant/willis-seafood-raw-bar
Best wood-fired pizza in the area. Located just 5 minutes from the house in Geyserville. Small place so definitely make reservations for dine-in and also does take-out.
www.diavolapizzeria.com
Used to be the Mardrona Manor. Located 5 minutes by car from the plaza. Absolutely beautiful inside and a cool bar (be sure to order the Estate Martini). Serving dinner and weekend brunch.
www.themadronahotel.com
Your vegan option in town. They feature a 100% plant-based restaurant, craft cocktails shop, coffee bar and more.
www.littlesainthealdsburg.com