Scopa
Hands down, this is our favorite spot in town for atmosphere and knockout Italian food. It’s very small and intimate, yet the bistro atmosphere is lively and electric. It’s right downtown on the plaza and always packed, but the food and ambience transport you into your own private world. Try the Tomasso’s Suga Calebrese for an amazing taste experience. Truth is we’ve never had a bad dish here; it’s impossible to go wrong. The food is simple but perfectly prepared every time. The staff is fantastic as well! Be sure to make reservations at least a couple weeks in advance. And if you can, check out Winemaker Wednesdays where local winemakers not only bring their best bottles, they actually serve you. It’s great fun!

http://www.scopahealdsburg.com
Check out the Zagat review: https://www.zagat.com/r/scopa-healdsburg

Chalkboard
This downtown eatery specializes in small plates inspired by what’s fresh on its three-acre organic garden located at Chalk Hill Winery. The stylish atmosphere is warm and welcoming. Everything on the menu comes a la carte. I ordered the steak on special that night, and when my plate arrived we were stunned to see a mere six bites of meat. But when Iwe took the first bite, it melted in our mouth. It was like nothing we’ve ever tasted before. Imagine smoky velvet — pure sensual delight! In a way, the small portion invited me to thoroughly enjoy each morsel. They have a terrific wine list and original cocktails too.

http://chalkboardhealdsburg.com/
Check out the Zagat review: https://www.zagat.com/r/chalkboard-bistro-wine-bar-healdsburg

Barndiva
Just off the square in downtown Healdsburg, Barndiva’s rustic décor and good vibe make for a perfect dinner for two. It’s a wine bar, cocktail lounge, art gallery and bistro all in one. If you can, get a table in the garden where the fountains and twinkling overhead lights create a charming atmosphere as evening settles. The food is out of this world. we strongly recommend the wine-pairing menu. The wines may have stood fine on their own, but it was the way they complemented the food that was so exquisite. The staff really knows their wine and food, so take their suggestions! The pours were generous, service excellent and the food fantastic.

http://www.barndiva.com
Check out the Zagat review: https://www.zagat.com/r/barndiva-healdsburg