3 Spectacular Rooftop Bars in Healdsburg

Written by Tracy Ellen Beard

October 11, 2022
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Rooftop dining elevates every dining experience. Here are some of our favorite rooftop bars in Healdsburg, embracing the best of California wine country.

Sipping a decadent cocktail or dining on delicious cuisine on a rooftop somehow elevates the experience to something luxurious and maybe even magical. Rooftop bars and restaurants are exceptional. Some have firepits that generate warmth and create cozy nooks, others boast 360-degree views that take your breath away, and almost all embrace the alfresco ambiance that makes people want to hang out for hours. To my surprise, on a recent trip, I discovered three unique rooftop bars in Healdsburg.



The Rooftop Terrace at Harmon Guest House

After a light day of wine tasting in the Dry Creek Valley, I stopped at The Rooftop Terrace at Harmon Guest House. I had never heard of the place, but the Senior Vice President of Sales, Edd Lopez, at Trattore Farms told me I should check it out. What a find! The Rooftop Terrace opened approximately four years ago and was the first rooftop bar in Healdsburg.

The Rooftop Terrace.

The Rooftop Terrace. Photo courtesy of The Rooftop Terrace at Harmon Guest House


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I arrived at Harmon Guest House, took the elevator up to The Rooftop Terrace, and met Sheila, the head bartender. Sheila has been there since the beginning, and the mural on the bar wall depicts her and her craft. Sheila went to work telling me about the bar, and when plied for cocktail and food suggestions, she offered me her favorites and the most popular options. Buildings in Healdsburg are far from skyscrapers, but the views of Fitch Mountain, the Sonoma hills, and downtown Healdsburg were lovely.

Sheila at The Rooftop Terrace at Harmon Guest House.

Sheila at The Rooftop Terrace at Harmon Guest House. Photo by Tracy Ellen Beard



The Vibe at The Rooftop Terrace

This bar had a quiet, after-work, relaxed atmosphere and a firepit to keep visitors warm on cool nights. It was only 5 pm when I visited, so the crowd was pretty calm while I was there. I’m sure that as the evening continued, the volume of chatter got livelier. However, the bar is only open until 8 pm every night. Sheila said they close early because guest rooms are located directly below the bar. On weekdays the hours start at 3 pm, and they open at 1 pm on weekends. The Rooftop Terrace features a variety of local wines and spirits. Chef Tom Mulligan prepares an assortment of scrumptious bites.

Sheila made me a refreshing Market Cocktail with cucumber, vodka, mint, lime, soda water, and agave. It was delicious. I watched her make several gorgeous, and I’m sure tasty, drinks for other guests.

Cocktails at The Rooftop Terrace at Harmon Guest House, a rooftop bar in Healdsburg

Cocktails at The Rooftop Terrace at Harmon Guest House. Photo by Tracy Ellen Beard

The Food is Phenomenal

Tom brought out several dishes for me to try. The Heirloom Heiress Tomato Salad was terrific. The watermelon, queso fresco, Spanish sherry vinaigrette, and diversity of tomatoes made a delicious salad, but the pickled summer squash elevated the dish to another level.

Heirloom Heiress Tomato Salad at The Rooftop Terrace at Harmon Guest House.

Heirloom Heiress Tomato Salad at The Rooftop Terrace at Harmon Guest House. Photo by Tracy Ellen Beard

The Local Lamb Birria Sope with handmade masa tortillas, queso fresco, pico de gallo, and spicy aioli were perfectly seasoned and possessed a beautiful eclectic array of flavors and textures.

Lamb sopas at The Rooftop Terrace at Harmon Guest House.

Lamb Birria sopas at The Rooftop Terrace at Harmon Guest House. Photo by Tracy Ellen Beard

If you are in the area, The Rooftop Terrace at Harmon Guest House is a must-stop. When you arrive or leave, take the stairs and check out the stunning bird murals on the walls.

Bird murals at The Rooftop Terrace.

Bird murals at The Rooftop Terrace. Photo by Tracy Ellen Beard

Roof 106 at The Matheson

Roof 106 sits above The Matheson restaurant, Chef/Owner Dustin Valette’s second successful restaurant in Healdsburg. The rooftop bar/restaurant boasts an indoor space with a large bar, numerous tables, and a Mugnaini wood-fired oven used to cook delicious small-plate dishes and other tasty options. Cocktails crafted at Roof 106 feature unique spirits, seasonal fruits, herbs, and flowers.

The wood-fired oven at Roof 106 at The Matheson.

The wood-fired oven at Roof 106 at The Matheson. Photo by Tracy Ellen Beard

Trees, greenery, and firepits augment the garden setting in the outdoor space overlooking the Healdsburg Plaza. Roof 106 is buzzing with activity. Whether you plan to enjoy a drink and small plate before dinner downstairs or spend the evening imbibing and noshing, you can’t go wrong.



Roof 106 at The Matheson.

Roof 106 at The Matheson. Photo courtesy of The Matheson

The Food and Drinks at Roof 106

Chef Brian Best has shaped the menu upstairs. Whether you are in the mood for a light dish of fried squash or something more substantial like a decadent pizza or steak from the wood-fired oven, he has something on the menu to tantalize your tastebuds. Signature cocktails are constantly evolving, and the staff puts the same effort into making creative and tasty non-alcoholic beverages.

Pizza at Roof 106, a rooftop bar in Healdsburg.

Pizza at Roof 106. Photo courtesy of Roof 106.

Early on a Saturday afternoon, my friend Judy and I stopped in for a cocktail at Roof 106 before dinner at The Matheson. Upon entering, we noticed that locals and travelers filled the tables. I stepped up to the horseshoe-shaped bar and ordered a Butterfly Authority, a colorful drink made of Buffalo Trace Bourbon, Madeira, blackberries, and thyme. The drink was slightly sweet with a touch of herbaceousness, a fabulous start to an exceptional dinner.

Cocktails at The Rooftop Terrace at Harmon Guest House, a rooftop bar in Healdsburg

Cocktails at The Rooftop Terrace at Harmon Guest House. Photo by Tracy Ellen Beard

Rooftop Garden at SingleThread

Step into the serenity and the luxury of the rooftop garden at SingleThread. This space is not only stunning and Zen but exclusive. The rooftop garden is reserved and available by reservation only for guests of the SingleThread Inn and for pre-dinner drinks for diners at SingleThread restaurant.

SingleThread rooftop, a rooftop bar in Healdsburg.

SingleThread rooftop. Photo courtesy of Eric Wolfinger

Inn guests have the most access to this one-of-a-kind rooftop space. They can have breakfast on the rooftop instead of in their rooms and enjoy the area at their leisure. Diners at the restaurant are welcome to reserve time on the roof for up to 30 minutes before their scheduled dinner reservation.

The rooftop is elegant and comfortable, with a firepit, well-designed heat lamps, well-appointed couches and chairs, and chic tables. The area is a working garden with herbs, fruit trees, and even a greenhouse. Each summer, the greenhouse is used to dry seaweed served in the restaurant.

SingleThread garden rooftop. Photo by Tracy Ellen Beard

The service on the rooftop is professional yet friendly. Guests are escorted up the elevator by a host and offered a selection of refined beverage options.

Rooftop bars in Healdsburg

Dom Pérignon at Single Thread. Photo by Tracy Ellen Beard

The Evening of a Lifetime

I brought a long-time family friend, Ken Kelly, to SingleThread for dinner. We shared a glass of bubbles on the rooftop before engaging in one of the top dinners of my life. Ken was an inspiration to me as a youngster. I grew up listening to stories of high-end hotels, fine dining, and delicious wines. Ken was in marketing and sales for a prominent corporation when I met him. He taught me about fine wine and graciously shared bottles from his library. It was my pleasure to take him to a dinner that surpassed my expectations and rose to the top of his list of dining experiences.

Ken Kelly and Tracy Beard.

Ken Kelly and Tracy Beard dressed for dinner at SingleThread. Photo by Judy Kelly

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Rooftop Bars in Healdsburg

Spend an evening enjoying fabulous drinks, wine, and memorable dishes at one of the three rooftop bars in Healdsburg, California. I have visited rooftop bars in Portland, Seattle, Barcelona, Paris, and more; they were all worth the visit. When planning your rooftop experience, check out more exciting destinations and delicious culinary travel opportunities on Wander with Wonder.

Rooftop dining almost seems magical. Here are some of our favorite rooftop bars in Healdsburg, embracing the best of California wine country.

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3 Spectacular Rooftop Bars in Healdsburg



Written by Tracy Ellen Beard

Tracy Ellen Beard, Wander With Wonder Senior Editor, is a freelance writer, editor, and photographer based in Longview, Washington. She is an avid traveler, wine connoisseur, foodie, hiker, cyclist, and kayaker. Tracy is the “Out and About” columnist for the Columbia River Reader and writes monthly for Upscale Living Magazine. She also contributes regularly to LuxeGetaways, Northwest Travel & Life, Country, Country Extra, and several other magazines. Her stories focus on luxury and adventure travel, fine dining, wine, libations, road trips, and recipes. Tracy shares a unique perspective on the world from her personal journeys and the excursions she took as the founder and past president of an international children’s nonprofit. Her twenty years of experience writing in various genres, and her culinary training in San Francisco, California, have added to her knowledge and expertise.

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