Healdsburg Windsor Loop
Healdsburg, California
Road
33 miles | 1,600 ft elevation
Healdsburg is located in Sonoma County in the heart of wine country. There are miles and miles of picturesque roads and the weather is near perfect all year long. This route takes you from Healdsburg through the outskirts of neighboring town, Windsor, and through the wineries of the Russian River Valley and Dry Creek Valley.
Starting near the Healdsburg town plaza, head east along the Foss Creek Pathway and over the Russian River along the Healdsburg Avenue bridge. For the next few miles, you’ll ride parallel to the freeway along the Old Redwood Highway. Around mile 4, take a right onto Starr Road where you’ll ride through a residential area before winding your way through the outskirts of Windsor.
You’ll reach a “T” in the road and continue west on Mark West Station Road, Trenton-Healdsburg Road and Eastside Road. These bumpy back roads will eventually lead to Wohler Road and the iconic Wohler Bridge. After crossing the Russian River (around mile 12), you’ll encounter a short climb up Westside Road, surrounded by lush vegetation and tall trees. After a brief descent, you’ll continue along rollers as you ride past a number of the Russian River Valley vineyards.
At mile 21, take a left onto West Dry Creek Road, a quiet, scenic road and enjoy the views of the Dry Creek Valley wineries for the next 5 miles. At mile 26, head east on Lambert Bridge Road, and in about half a mile you will reach the Dry Creek General Store, a popular stop and a great place to grab a snack.
After leaving the store, head south on Dry Creek Road for about a mile and make a sharp left turn up Lytton Springs Road and continue to climb as you make your way along Chiquita Road. Once you make the descent to Grove Street, hop on the Foss Creek Pathway for the final mile back to the plaza.
For more routes from Healdsburg, see the Healdsburg landing page.
Strava Route:
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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