Where to Ride
Healdsburg is my favorite place to ride in California. It is located in northern California’s wine country (in Sonoma County) in the middle of Alexander Valley, Russian River Valley and Dry Creek Valley. You will spend miles riding by countless wineries and vineyards, and the weather is near perfect all year long.
Start your ride from the heart of Healdsburg (near the plaza) and head north towards Alexander Valley Road. Once you leave town, you will make your descent into Alexander Valley and be greeted by sweeping views of countless grapevines. After passing the Jimtown Store (which is currently closed), you have a few route options. You can go straight and climb Pine Flat Road (out and back); you can head south (on 128) and do the Chalk Hill Loop; or you can go north (on Red Winery Road) towards Geyserville and do the Dry Creek Loop.

The Geyserville option is a leisurely route with minimal climbing, and it takes you through Alexander Valley and Dry Creek Valley. The Dry Creek General Store is a popular stop and a great place to grab a snack. From there, take Lambert Bridge Road to West Dry Creek Road, a quiet and scenic way back into town.
The Chalk Hill Loop offers some nice climbing as you ride through Alexander Valley and Russian River Valley. After crossing Wohler Bridge (over the Russian River), enjoy the shaded roads below the tall redwood trees and the many picturesque wineries as you head back into town on Westside Road.
If you’re looking for a more challenging route, test your legs on Geysers Road. Take West Dry Creek Road out of town and head north towards Cloverdale. After you cross the Russian River (about 21 miles into the ride), you begin your ascent up Geysers Road. The road will be narrow (and rough in spots) for about 12 miles until it turns into a wider two lane road. At this point, prepare for some steep sections as you continue to climb. You will be rewarded with some epic views and a short descent until you reach another sharp climb. Around mile 42, you make the final 4-mile descent back to the valley floor. Enjoy the sweeping views, the cows in the pastures and the mostly-flat final 10 miles back into town.

Strava Routes:
Healdsburg to Geyserville and Dry Creek Loop
Healdsburg to Geyserville with Pine Flat Rd Climb
Healdsburg to Chalk Hill and Russian River Loop

Where to Stay
Harmon Guest House – this chic, modern hotel is located in the center of town, near Healdsburg Plaza, and is within walking distance to many restaurants, wine bars and shops. The hotel is bike friendly and the rooms are spacious and comfy. The highlight of this property is The Rooftop, where you can admire the views while sipping on wine (or a cocktail) and enjoying a bite to eat.
Hotel Trio Healdsburg (by Marriott) - this hotel is located 1 mile north of Healdsburg Plaza, and in my opinion, is the perfect place to stay during a wine country bike trip! The rooms are suite-style and come with a fully equipped kitchen. They offer a free breakfast (that's actually good!) and their large outdoor patio and pool are perfect for soaking in the sun after a long ride. It is located right next to the Foss Creek Pathway, which makes it easy to walk or ride into the heart of town (about a 25 minute walk or 7 minute ride), or you can take the hotel's free shuttle.
Healdsburg is known for its farm-to-table restaurants, artisan bakeries, and local wine bars; so, enjoy your time in this quaint town!

What to Know
The best place to park for free and for several hours is along Vine Street, across from the Safeway (plus, the bathrooms in Safeway are clean). The City of Healdsburg website has more info on parking, including EV charging stations.
Weather is great for riding all year long, but can get hot in the summer and is sometimes affected by “fire season”.
Weekend afternoons can be busy with cars as people drive to nearby wineries. You may want to plan accordingly so your ride ends by early afternoon.
The patio at Healdsburg Bar & Grill is a great post-ride spot for some food and nice ambiance. It’s casual and you can bring your bike on the patio. 
Explore the town off-bike! There are many cute shops and places to pop-in for a snack.
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