Chalk Hill Loop
Healdsburg, California
Road
53 miles | 2,200 ft elevation
Chalk Hill Loop is a quintessential Healdsburg ride, offering some nice rollers through the Russian River Valley, climbing and descending into the Alexander Valley and picturesque vineyard views through Dry Creek Valley as you head back into town.
Starting near Healdsburg plaza, head west out of town and make your way down Westside Road through the Russian River Valley. About 10 miles into the ride, you will ride along Wohler Bridge, crossing over the Russian River. Wind your way along Eastside Road and Mark W Station Road as you make your way into the town of Windsor via Shiloh Road.
Around mile 18, you’ll head north up Faught Road and soon make your way up Chalk Hill, a gradual climb up and fun descent down. Chalk Hill Road comes to an end around mile 28, intersecting Route 128 and leading you into the Alexander Valley. For the next 11 miles, you’ll roll over rough roads and some smooth sections as you make your way into the town of Geyserville (a nice place to refuel).
About a mile out of town, head west up Canyon Road and you’ll soon descend into the Dry Creek Valley. Cross over Yoakim Bridge and head south on West Dry Creek Road. The next 9 miles are scenic with some rollers as you ride by countless vineyards. You will find yourself back at Westside Road (where you started your day) and take it back into Healdsburg for the final mile.
For more routes from Healdsburg, see the Healdsburg landing page.
Strava Route:
Alternative short route (in reverse):
Hotel Recommendation
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!
Notes
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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