Hotels & Activities

Lodging

Hotel Healdsburg

25 Matheson Street
Healdsburg, CA 95448

Dry Creek Inn

198 Dry Creek Road
Healdsburg, CA 95448

Hotel Trio

110 Dry Creek Road
Healdsburg, CA 95448

Shuttles will be provided to and from Harper’s Rest; Limited self-parking available. Shuttle locations and departure times provide on the Home page.

While You’re Here

Please check out these sample itineraries to help you make the most of your time in Healdsburg!

  • Coffee & Breakfast

    • Flying Goat Coffee - best espresso in town right on the square

    • Costeaux French Bakery - pastries, breakfast sandwiches, and full-service breakfast menu

    • Plank Coffee - Great coffee and breakfast near Hotel Trio and Dry Creek Inn

    • Black Oak Coffee - off the square, another great coffee option

    • Quail & Condor - excellent coffee, pastries, and bread from the New York Times-recognized, 2025 James Beard semi-finalist for Outstanding Bakery

    • The Parish Cafe - NOLA-style breakfast with beignets

    • Acorn Cafe - delicious breakfast or lunch with award-winning pancakes and avocado toast

    • Carmella - fresh, plant-based smoothies, juices, and nourishing bowls

    Shopping & Food

    • Healdsburg Plaza - the historic town square surrounded by locally-owned boutiques, galleries, and specialty shops

    • Noble Folk Ice Cream & Pie Bar - house-made artisan ice cream and seasonal fruit pies, perfect for an afternoon treat

    • Dry Creek General Store - beloved country store and lunch destination with deli sandwiches, outdoor seating, local wines, and provisions (ideal bike ride stop)

    • Troubadour - excellent sandwich shop from the team behind Quail & Condor

    • Journeyman Meats - butcher shop and sandwich counter specializing in house-made charcuterie and premium meats

    • Levin & Company - independent bookstore with carefully curated selections and upstairs art gallery featuring rotating local exhibitions

    • Forager - modern mercantile with thoughtfully chosen home decor, linens, drinkware, and lifestyle goods

    • Maison Smith - elegant home goods and decor with a sophisticated aesthetic (sister location in Santa Fe)

    • Maison Fiori - fresh flowers and curated home accessories

    • Bon Ton Studio and Bon Ton Baby - contemporary women's and children's clothing and accessories

    • Christy Lyn - women's clothing boutique by Houston-based designer

    Art Galleries

    • Gallery Lulo - contemporary jewelry, sculpture, and art from emerging and established national and international artists

    • The Harris Gallery - fine art photography and contemporary works, featuring both local and internationally recognized artists

    • Aerena Gallery - curated collection of contemporary paintings, sculpture, and mixed media from regional and national artists

      Levin & Company - independent bookstore with upstairs art gallery showcasing rotating exhibitions from local artists

  • Estate Experiences:

    • Stonestreet Estate - mountain wines with dramatic valley views and intimate tastings

    • Ridge Vineyards (Lytton Springs) - legendary Zinfandel from one of California's most respected producers, stunning mountaintop setting

    • MacRostie Winery (Estate House) - A Healdsburg staple known for its stunning hilltop views over the Russian River Valley and some of the Sonoma Coast's finest Chardonnay and Pinot Noir

    • Silver Oak - renowned Cabernet Sauvignon, stunning modern architecture

    • Jordan Vineyard & Winery - iconic estate, world-class Cabernet

    • Rickards Vineyard - family-owned, genuine hospitality, off-the-beaten-path

    • Francis Ford Coppola Winery - movie memorabilia, pools, family-friendly

    • Dutcher Crossing - approachable wines, bocce ball, picnic-friendly

    • Stuhlmuller Vineyards - estate-grown wines, personal service, Alexander Valley

    • Mazzocco Sonoma - relaxed atmosphere, beautiful grounds, great for groups

    Tasting Rooms on the Square:

    • Marine Layer Wines - cool coastal-inspired wines on the Square

    • LIOCO Wine Co. - bright, airy space with good Pinot and Chardonnay

    • Idlewild Wines - Italian and Rhône varietals with a creative, welcoming vibe

  • Explore wine country the best way possible — on two wheels. Whether you're up for a leisurely pedal to the Dry Creek General Store or tackling the rolling hills of West Dry Creek Road, Healdsburg's scenic routes are made for biking.

    Check out Henry’s curated Strava routes below

    Where to rent (electric options available):

    • Spoke Folk Cyclery

    • Wine Country Bikes

  • Not everything in wine country involves a tasting room. Here are some of our favorite ways to mix it up:

    Hit the Trails:

    • Fitch Mountain Loop - 3-mile hike with panoramic views of the valley (moderate effort, big payoff)

    • Armstrong Redwoods State Natural Reserve - 15 minutes away, walk among ancient redwoods

    • Healdsburg Ridge Open Space - easy trails with wildflowers in spring

    Get on the Water:

    • Russian River Adventures - kayak or canoe down the Russian River, mellow float through redwoods

    • Schoolhouse Beach - local swimming spot with river access and sandy beach

    • Lake Sonoma - 15 minutes away, paddleboard or find a quiet cove for swimming

    In Town:

    • Saturday Farmers Market - May through November at the new Foley Family Community Pavilion, browse stalls of just-picked produce, handmade pasta, local olive oil, and cut flowers. Arrive early for the best selection.

    • Healdsburg Center for the Arts - rotating exhibitions, local artists, free admission

    • Happy hour on the Plaza - Duke's for cocktails, Bravas for tapas, Willi's for wine and small plates, The Harmon House Rooftop, or Rooftop 106 at the Matheson