Friday: Check in at Montage Healdsburg and just chill.

Check in: Montage Healdsburg

Pull off the road and wind your way up to the entrance of Montage (100 Montage Way), the luxurious resort that opened in January 2021. But beware: You might want to stay forever. Once you've checked in, there’s really no need to leave. The 130 bungalow-style guest rooms are all perched organically upon the oak-studded hills and have amenities like soft robes, soaking tubs, outdoor showers, and private patios (some with fire pits). The decadence picks up momentum with hot tub dips, cocktails fireside, massages, and delicious bites at every turn. The main nexus of buildings is home to the Scout Field Bar, Hazel Hill restaurant, Healdsburg Country Store, Spa Montage, fitness center, pool, and a seasonal pool bar. The surrounding vineyard, planted and overseen by lauded winemaker Jesse Katz of Aperture Cellars, will eventually supply the grapes for a special house label of wines.

Bikes, Hikes, Bows + Arrows

A unique onsite opportunity awaits at Compass Sports, an outpost up the hill from the Montage lobby that serves as ground zero for adventures. A variety of bikes and e-bikes are available for rent, including some with little wooden wagons perfect for lugging your picnic basket or that case of wine.

Montage guests can also opt in for a complimentary archery session with a guide, featuring hand-crafted bows and arrows made just for the hotel using traditional methods and natural materials by master craftsman Victor Kühn. From the target area, you’ll have a lovely view of the beehives perched on top of the hill.

If you are up for a bigger excursion, the hotel has partnered with Adventure IO to offer a roster of day trips and activities including bee-lining (the safe capture and identification of bees) with the resort’s resident beekeeper Candice Koseba (founder of Sonoma County Bee Company) to a helicopter ride with Butterfly Aviation over Sonoma County, ending with a private wine tasting experience. All of this can be booked directly through the concierge.

Lounge around.

It’s always nice to see a hotel lobby actually utilized. And this one, with plush furnishings and a myriad of seating configurations, is a great place to chill after adventuring. The Scout Field Bar, offers a tidy menu of upscale cocktails like the surprising and favorite John Chapman, made with a base of sherry cask-aged Source One vodka and topped with Thai coconut foam and crisp dehydrated apple slice. Go ahead and order some truffle fries, because you know you want to.

Dinner at Montage's Hazel Hill

This lovely, low lit dining space is headed up by chef de cuisine Jason Pringle, who brings a bit of European sensibility to the seasonally changing menu. Dishes might include the astounding smoky sturgeon with kaluga caviar and fried beet ribbons or saffron chittara pasta with Dungeness crab. The house-made olive epi rolls are served with an amazing little pot of butter sprinkled with salt, and sommelier Petra Polakovicova’s list will guide you in the right direction. Desserts don’t disappoint thanks to the deft hand of newly appointed pastry chef Devin McDavid. Don't miss the sensuous Greek yogurt panna cotta with white verjus sorbet.

Saturday in Healdsburg: Art First, Then Drinks on the Plaza

Catch a ride.

One added perk to staying out at Montage Healdsburg is their partnership with Cadillac. Being the official “house car” means that guests can catch a free ride to and from Healdsburg Plaza, leaving the driving to someone else while you partake in the fun. The Plaza is a lovely zone, utilized by visitors and locals alike as any good town square should, with a host of food, drink, art and shopping options fanning out on all four sides. You can easily spend a day here.

Shop around.

There’s no shortage of shops to bop into here, and a cool place to start is at Bon Ton Studio(120 Matheson St.), where founder Erika Dawkins curates a cushy selection of artisan textiles and home goods. And while this little shop is a couple of years old now, she recently added a second location across the way called Bon Ton Baby (107 Plaza St.), just as she added a second child to her own family. That's where you will fall in love with every tiny, soft, fuzzy, soothing-colored thing you see, even if there isn’t a baby in your life.

Art Walk

There are almost as many galleries in Healdsburg as there are tasting rooms, and it’s fun to break up your shopping stroll by stopping to gaze at some art. At the just-opened Legion Projects(711A Healdsburg Ave.) north of the Plaza, former fashion journalist turned artist Sydney Pfaff is curating modern art works with shows that rotate every few weeks. // in a historic building that was once a bank, you’ll find The Harris Gallery(320 Healdsburg Ave.), where two generations of artists, M.C Harris (dad) and A3L3XZAND3R (son, formerly known as Alex) has created a community hub that really indicates how Healdsburg, despite being a buzzy Wine Country getaway, is still a small town with a tight network of locals. Leah Harris (A3L3XZAND3R’s wife), just launched a wine program onsite, partnering with winemakers such as Wells Guthrie and Leo Hansen (of Leo Steen), to offer fights and glasses of impressive, custom-made wines enrobed in various Harris family art labels. This isn’t your grandmother’s white zinfandel at the art fair.

Lunch at Troubadour

There is some evidence that upscale sandwich shops are trending right now, and if you want to try one of the best examples of carefully sourced ingredients creating a perfect end result, definitely don’t miss Troubadour(381 Healdsburg Ave.). Owners Melissa Yanc and Sean McGaughey, both former chefs at the nearby Michelin-starred restaurant SingleThread, have just opened this shiny new space with a menu of classics, rotating specials, and a few sides. You’ll find creamy egg salad on thick slabs of milk bread and warm pastrami with caraway kraut on superseed loaf. The butterscotch pudding capped with chocolate ganache is earth-shattering. Also advisable is to walk a few blocks down to their sister bakeshop, Quail & Comdor, to grab treats like a chocolate tahini croissant or yuzu cream–filled morning bun. Seating is pretty limited onsite at Troubadour, with no outdoor seating, so it makes perfect sense to take your goodies to go and enjoy them al fresco on a bench at the Plaza.

Wine!

Some people would say that wine is the true reason to visit this place, with a unique placement at a central joint of Northern California Wine Country. And there certainly are plenty of great specimens to be found here, from historic estates to small production micro-labels.

Marine Layer(308B Center St.) is a newcomer in a sleek yet cozy tasting room on the Plaza, designed by the local duo at Hommeboys. You’ll taste through a concise list of cool-climate Sonoma Coast wines and have the opportunity to sample some plant-based mezze (apple tahini, beet hummus, fafda crackers) from Little Saint(25 North St.), an exclusive sneak peek, so to speak, from the highly anticipated restaurant that is yet-to-open in the former Shed space. // Around the corner sits the Idlewild tasting room (132 Plaza St., by appointment), an outpost for Mendocino-grown, Piedmontese-inspired natural wines. You'll also find a few selections from fellow natural wine stars Ruth Lewandowski and Jolie-Laide. Pull up a sidewalk chair for a sip and a salumi plate. // Aeris(337 Healdsburg Ave.) is the newest addition to the Plaza wine world. This exciting project was launched by the pinot noir masters of Rhys in the Santa Cruz Mountains, who undertook an astounding task of planting Mount Etna varieties (carricante and nerello mascalese), never before grown in California, on a unique ridgetop site called Centennial Mountain in Northern Sonoma County.

Cocktails for Dinner

When a team of friends and restaurant professionals with over 25 years experience finally open their own thing, this is it. Lo & Behold(314 Healdsburg Ave.) is the suitably named debut from cocktail pioneers Laura Sanfilippo and Tara Heffernon. As expected, the drinks are the stars, with concoctions like the Phatty Margarita (avocado and coconut oil–washed tequila) and the Snap Back (gin, cucumber, snap peas, cardamom, and mint). You will want to drink many of these. They have partnered with chef Sean Raymond Kelley who offers a fun menu of equally exciting dishes like the tempura-fried Son-in-Law Eggs and the Winter Greens with house-made pierogi and sesame brown butter. It’s comfort food with a global sentiment.

Sunday: The Lazy Wine Road Home

Bacchus Landing

On the outskirts of downtown Healdsburg sits a new compound called Bacchus Landing(14210 Bacchus Landing Way). Unveiled in July 2021 by siblings Monica and Francisco Lopez along with their parents Al and Dina, this family-run spot is equal parts event venue, wine tasting complex and gathering space, with a square-shaped plaza reminiscent of piazzas and zocalos around the world. Tasting rooms onsite highlight the family’s own wine label, Aldina, as well as wineries including 13th and Third, Dot Wine, Montagne Russe, and more. Each tasting space is surprisingly different from the next, offering an array of unique experiences. There's also a market with a variety of snacks and drinks that you can enjoy in the picnic area complete with bocce ball courts, lawn games, and a rotating schedule of live music.

Aperture Cellars

As you depart town and head South toward Windsor, stop at Aperture Cellars(12291 Old Redwood Hwy), a stunning architectural gem, inspired by the physical aperture of a camera, where young winemaker Jesse Katz, son of famous photographer Andy Katz, makes memorable Bordeaux-style wines from Anderson Valley. He has planted some of the variety onsite, led by his prediction that our changing climate will mean that Sonoma County will one day soon make noteworthy cab. He is also well known for his other label, Devil Proof, Wine Advocate's highest-rated Californian malbec of all time.

Don’t Leave

By now, maybe you just want to call in sick and stay one more night? It’s certainly tempting, given all the things you still have yet to try. The Harris family will tell you not to miss Asahi(335 Healdsburg Ave.), the small sushi spot that recently opened across the street from the gallery. If you can go on a Tuesday night, you'll get the benefit of fish straight off the plane from Tokyo's legendary Tsukiji Market. Later this spring, The Madrona(1001 Westside Rd.), a historic boutique hotel that's been redesigned by Jay Jeffers, will reopen in the heart of Healdsburg, along with Little Saint and Maison Healdsburg, a wine bar and shop from another SingleThread alum.