As a local to the Healdsburg and Windsor area, I love being able to stay local for awesome food, wine & cocktails. We all love Happy Hour, and knowing which spots are the best to go to for it. Follow along for the Best Healdsburg Happy Hours.

Healdsburg Happy Hours:

Arandas Restaurant

The newly established Arandas in Healdsburg has quickly become one of my top picks for Best Mexican Restaurants in Healdsburg thanks to its beautiful interior, fabulous food, and fantastic hospitality.

Don’t miss their dynamic happy hour from Monday to Friday, 4-6pm, featuring $5 margaritas that perfectly complement the vibrant flavors of their menu. Enjoy your meal on the beautiful patio space, where every dish tells a story, and every moment adds to an adventure worth sharing. Visit Arandas in downtown Healdsburg for a culinary journey like no other.

Photos courtesy of Arandas Restaurant in Healdsburg

Bravas Bar de Tapas

If you’re looking for a great setting and outdoor bar, Bravas has one of the best happy hours. Whether you want a casual bite (tapas) of killer cocktails Brava’s is a great spot for both in Healdsburg. Happy Hour is 3:00pm-6:00pm Sunday through Thursday, be sure to check out some of their great deals. 420 Center St, Healdsburg, CA 95448

The outdoor back patio bar is my favorite with divine cocktails and tasty bites to pair with them.

Photo Courtesy of Bravas Bar de Tapas

Bravas is also featured on my blog, The Best Cocktails Bars in Healdsburg to Try.

Chalkboard

Chalkboard has a fantastic happy hour that runs Sunday to Friday from 4:30pm-6:30pm. Order anywhere from their delicious pasta of the day, to their famous meatballs, or a limoncello drop of spritz! Enjoy some great food and service at this Healdsburg hotspot. 29 North St, Healdsburg, CA 95448

Photo Courtesy of Chalkboard Healdsburg

Dry Creek General Store’s Bar

One of my favorite parts of a day trip to Healdsburg, aside from the wine tasting of course, is visiting the Dry Creek General Store. Talk about a small town bar with a lot of character. This is it! Be sure to check it out on your way out of Healdsburg as it’s the perfect pit stop after a day of wine tasting before heading back home.

They have a happy hour every Monday & Tuesday from 2pm to 4pm. $5 Draft Beers, $10 Wine, $5 Hot Dogs. 3495 Dry Creek Rd, Healdsburg, CA 95448

Harmon Guest House Rooftop

The Harmon Guest House Rooftop is truly one of a kind. Not only does it have a beautiful view of the Healdsburg area, but has amazing food and drinks. Stop by Monday’s for $1 Oysters, and their other happy hour specials, including a rooftop taco and shrimp tostadas. 227 Healdsburg Ave, Healdsburg, CA 95448

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Portraits by Ashlyn Kudransky, Hotel photos courtesy of Harmon Guest House

All smiles during a Happy Hour at the Harmon Guest House.

This is one of their amazing appetizers. Hard to beat fabulous cocktails and fresh shrimp cocktail. Perfect rooftop location in downtown Healdsburg.

Little Saint Healdsburg

The cafe and lounge at Little Saint Healdsburg is definitely a go-to for locals to meet up for good coffee, breakfast, pastries, lunch and dinner. The cafe and lounge area transitions into a cool cocktail lounge and wine bar at night, so you can enjoy breakfast and happy hour all at the same amazing spot.

As of most recently Fall of 2023, there is a Happy Hour at the Little Saint with cocktails, light bites from 3-6pm. See menu and a preview of the Little Saint Happy Hour below!  25 North St, Healdsburg, CA 95448.

Even the mocktails are delicious at the Little Saint Happy Hour.

The Matheson Healdsburg

Whether you’re seated inside Roof 106 or outside on the rooftop taking in the beautiful Healdsburg views… you’re in for a treat. The happy hour at the Matheson Ground Floor bar is a great one to try in the area! Enjoy snacks like empanadas, beef tartare, and charcuterie boards, or crafted pizzas and burgers. 4-6pm throughout the week! 106 Matheson St, Healdsburg, CA 95448

Read more about The Matheson Healdsburg on my blog!

The NEW Matheson Bar Happy Hour is amazing. It’s offered Tuesday – Saturday from 4:00 – 6:00 pm at the ground floor bar (not the rooftop bar).

The Matheson Burger is hands down one of the BEST in Healdsburg. Check out my Guide for the Best Burgers in Healdsburg on the blog here. 

The amazing Pizza from Roof Top 106 is also featured on the happy hour menu in smaller sizes.  You really can’t go wrong with whatever you order at the Matheson’s Happy Hour.

PizZando

PizZando is an incredible pizza spot for those of you looking for some tasty pizza in Sonoma County. This restaurant is a Healdsburg gem that overlooks the historic Healdsburg plaza and is the perfect place to enjoy its rustic menu of wood oven pizzas. The happy hour here is Monday-Friday from 3pm-5pm. 301 Healdsburg Ave, Healdsburg, CA 95448

Read more about PizZando in The Best Pizza in Healdsburg blog post!

Spirit Bar at Hotel Healdsburg

The Spirit Bar at Hotel Healdsburg has an amazing happy hour you have to try. You can enjoy light bites and burgers, along with an array of cocktails, wines and beers. Happy Hour at the Spirit Bar is daily from 4:00pm-7:00pm. Hotel, 25 Matheson St, Healdsburg, CA 95448

Photo Courtesy of Hotel Healdsburg

Taste of Tea

The Taste of Tea is a Japanese classic with a modern twist. They also have tea-based sake cocktails that you should definitely sneak into your meal during brunch. 109 North St, Healdsburg, CA 95448

Take a look at their Happy Hour Menu below!