I’ve always believed that autumn in wine country feels more alive than summer. There’s a crispness in the air, a whispered urgency in each vine, and a kind of alchemy when grapes are pressed, kitchens shift into root-vegetable mode, and towns like Healdsburg glow in ochre and auburn light. This October, we carved out four days and three magical nights at Hotel Healdsburg, enveloped in their On the Town Harvest experience — and it remains one of those escapes that lingers in memory.
Dallas to Healdsburg is such and easy journey made simple by the direct flight that American Airlines offers from DFW to Santa Rosa Charles M. Schulz airport. You depart in the morning and you're in Healdsburg in time for lunch. Simply rent a car for exploring or you can UBER like we did. It's only a 20 minute drive to Healdsburg. Pulling into the small-town plaza feels like stepping into a dream. Hotel Healdsburg sits on the central square, tucked quietly but centrally placed. Its design is that exquisite balance of refined minimalism and warm agrarian charm — a beautiful blend of light, texture, and calm. I was greeted with a quick check-in and keys to a gorgeous suite that struck me instantly as “home for the next three nights.” The scent of olive groves, faint stone, and wood framed the moment perfectly.
The Heart of the Package: On the Town Harvest
The concept behind the On the Town Harvest offer is simple and yet richly layered: a two-night stay, $100 property credit to spend at the hotel (spa, dining, bar) and a $100 On The Town credit to use with independent tasting rooms, shops, and restaurants in downtown Healdsburg. Morning breakfasts are included, as is valet, access to pool, spa, fitness, bikes, and more. We used the hotel credit for a couples massage at the Spa, which was lovely. The "on the town" credits were used to explore restaurants, experiences and the stores detailed below. We decided to extend our stay with a three-night stay but you can adjust according to your plans. We upgraded and stayed in the Plaza Suite which was divine! Daily breakfast is included in this offer.
What we loved most: the hotel trusts you to explore. Show your receipts, and your On The Town credit is applied at checkout. It encourages wandering, tasting, impulse purchases of honey or olive oil, or stumbling into a gallery that catches your eye. FYI - Everything is walkable and on the plaza. It's so easy to explore!
Our recommendations (from this trip)
EAT:
SHOP & DO:
WINERY:
- Jordan Winery - we did the "Paris on the Terrace Harvest Lunch" and wine tasting. This is a delicious four course meal and wine pairing prepared by Executive Chef Jesse Mallgren. We're no strangers to this winery. More HERE. Jordan Winery is about a 15-20 minute drive from Healdsburg. It's easily our favorite winery in Sonoma County.
Why This Experience Resonates (and Why It’s Worth a Trip)
-
Curated but open: The On the Town Harvest package gives you structure (credits, included nights) but leaves your itinerary flexible. You choose your adventure.
-
Immersion over passivity: The Hands-On Harvest experience isn’t a spectacle—it’s a chance to become part of the story.
-
Gateway to small businesses: Using downtown credit encourages exploration of local shops, not chain stores. It’s economic and emotional support of the place itself.
-
Season-forward cuisine & wine: You taste the season everywhere—kitchen, glass, palette.
-
Design + comfort: The hotel’s spaces (pool among olive groves, the calm spa, luminous light) allow you to rest deeply between explorations.
-
Sense of discovery: Because everything is walkable, dreamy surprises await around corners.
Tips & Notes Before You Go
-
Book well ahead. Harvest season fills up fast.
-
Ask for a room with a great view. Even better, upgrade to a suite! We stayed in the Plaza Suite.
-
Use your $100 On The Town credit as you go: a little every day. Show receipts to the front desk.
-
Bring comfortable walking shoes, a camera, and curiosity.
-
Inquire about spa reservations early; we booked these before we got there.
-
If possible, align your stay with grape-pick or crush days—those are extra special.
-
Everything in town is walkable. Take your time. Stroll.
Our four days/three night stay was perfect for us. The On the Town Harvest banner reminded me what travel is supposed to feel like: rooted, generous, inspiring. It’s not about checking boxes. It’s about tasting, touching, wandering, daydreaming. Taking your time. Reconnecting.
Healdsburg, in autumn, is at its richest: human, farmed, artistic. Hotel Healdsburg offers a portal into that. I left feeling full — not just from food or wine, but from connection, narrative, and a deep sense of place. If you’re looking for a stay that is gentle, spirited, and deeply rooted in Sonoma’s soul, this is it.
xoxo - Tanya and Pete
P.S. On The Town - Season To Sparkle will run November 15-December 30 at Hotel Healdsburg. What a spectacular trip to plan during the holiday season!
our packing list
pin this image
