August 14, 2025 (Healdsburg, CA) — As the fall harvest season arrives in Sonoma County, Hotel Healdsburg, a luxury boutique property located on the historic Town Plaza, invites travelers to experience Healdsburg at its most vibrant through its new autumn experiences and “On The Town” package, designed to connect guests directly with the shops, restaurants, galleries, and tasting rooms located right outside the hotel’s front door.
“Healdsburg truly comes alive in autumn,” says Circe Sher, co-founder of Piazza Hospitality which developed and manages Hotel Healdsburg and its sister properties h2hotel and Harmon Guest House. “There’s an energy in the air, from the crush of grapes to the creativity of the local artists and chefs. With Hotel Healdsburg’s On The Town package and the new autumn experiences, we celebrate that spirit and help our guests connect to the region. On The Town is about stepping out the door and into the cultural fabric of Healdsburg.”
On The Town – Harvest Season Package: A Celebration of Healdsburg’s Downtown Scene
Available from September 1 through December 15, 2025, the On The Town package includes a two-night stay, a $100 property credit for dining and spa treatments at Hotel Healdsburg, and a $100 On The Town credit to use at nearby tasting rooms, boutiques, cafés, and other locally owned businesses.
Guests are encouraged to explore at their own pace, visiting shops filled with handmade goods, sampling olive oils and small-lot wines, strolling through galleries, and dining on menus bursting with autumnal ingredients, such as squash, persimmons, and heirloom tomatoes. Receipts from independent businesses within walking distance of the hotel are tallied at check-out and up to $100 is credited back to the guest’s final bill.
Fall Experiences: Wine, Art, and Nature
Hotel Healdsburg has also debuted new fall experiences created in collaboration with local partners. These offerings are only available to guests of Hotel Healdsburg and are designed to showcase the region’s harvest season from different perspectives, from hands-on winemaking and open-air painting to hiking through vine-covered hills.
The Hands-On Harvest Adventure at Zialena Winery offers guests the opportunity to experience grape harvest in all its sensory glory. A private golf cart tour leads through estate vineyards in Alexander Valley, with opportunities to help sort fruit, observe fermenting tanks, and if the moment is right, even participate in grape picking and stomping. The visit concludes with wine tasting and a picnic lunch by Dry Creek Kitchen, enjoyed among 2,500 hand-pruned vines. The experience is offered September 1 through November 15 for $200 per person and must be reserved 7 days in advance.
Art lovers can reconnect with their creativity by booking the En Plein Air Vineyard Painting Class, led by local artist and Healdsburg Art Atelier founder Nella Rubinstien. Set at MartaronaFamily Winery in Dry Creek Valley, guests can choose from different backdrops and environs, from hillside grapevines to a shaded creek. They also choose a preferred technique – acrylic, watercolor, or even watercolor flow (painting with meditation). This two-hour class includes all supplies, artistic guidance, and a tasting of wine and olive oil. Optional gourmet picnic lunches can be added. The experience runs August 15 through November 15 and is $400 for two guests or $600 for four.
For a more active connection to the landscape, theFall Foliage Hikes offer a custom-guided walk through Bella Vineyards, led by the region’s renowned trail guide and certified health coach Karen Austin. Along the way, guests learn about the local flora and terroir before enjoying a wine tasting and picnic lunch overlooking the valley. Hikes are available September through November (excluding October 6-14), with rates starting at $320 for two guests.
A Boutique Destination in the Heart of Healdsburg
Hotel Healdsburg has served as a cultural cornerstone in Sonoma County Wine Country since its inception in 2001, offering a deeply rooted, community-connected hospitality experience.
“We always believed that the best wine country experiences are the ones that offer a sense of place,” Sher says. “Whether you’re out in the vineyard or walking to a gallery down the street, our goal is to give guests a connection to the land, culture, and people that make Healdsburg special.”
The hotel features 50 elegantly appointed guest rooms and six suites, a 3,000-square foot spa, a 60-foot outdoor pool, Charlie Palmer’s acclaimed Dry Creek Kitchen, and the Italian trattoria PizZando. Guests enjoy a host of complimentary amenities, including continental breakfast, valet parking, in-room snacks, bike rentals, and personalized concierge services.
For reservations or more information on fall experiences and offers, visit www.hotelhealdsburg.com.
About Hotel Healdsburg
Reflecting the town’s distinctive wine country ambience and gentle rusticity, the three-story Hotel Healdsburg features 50 handsomely appointed guest rooms and six suites, a 3,000-square-foot spa, a 60-foot outdoor pool, country gardens within the grounds, and Charlie Palmer’s internationally renowned Dry Creek Kitchen. Hotel Healdsburg is located at 25 Matheson Street at the corner of Healdsburg Avenue on the western edge of the Healdsburg Town Square. Hotel Healdsburg can be reached by phone at (707) 431-2800 or toll free at (800) 889-7188. Learn more on the Hotel Healdsburg website: www.hotelhealdsburg.com.
