By Kathy Chin Leong
Locals never considered their small, pass-through community a tourist attraction, but agricultural towns are suddenly in. Ever followed a cheese trail? Or watched hops being added during beer fermentation? Stick a map pin on Windsor, California, your next great beverage and food destination. Approximately 90 minutes north of San Francisco, this enclave rivals hotspots in Napa at a fraction of the cost. Another bonus is fewer crowds.
Where to start? Sip and savor with this three-day itinerary:
DAY ONE
10 a.m. Hit the Windsor Chamber of Commerce and Visitors Center, found in the Windsor Depot. Ask a staffer to help you navigate the list of some fifty restaurants and thirty wineries, and tasting rooms. With three regional and nineteen community parks, activities such as hiking, bicycling, and paddling seem endless. Favorite public events include the Sunday farmer’s market, bi-annual wine walks, and Charlie Brown Christmas Tree Grove with over 200 trees decorated by groups and charities.
11 a.m. Sample wines under the Russian River Valley appellation, known for chardonnay and pinot noir. Foppiano Vineyards, under new ownership, boasts a refreshed picnic lawn, tables, landscaping, and overall improvements.
With a vision reimagined, the winery is entering a new era. On a warm day, imbibe outdoors and order a four-glass flight of Favorites for $25 or the Best of the Blocks for $30. Purchase cheese and nibbles on the spot or order a box lunch. Foppiano offers a 2021 Reserve Carignane. If you are new to carignane like we were, you can experience this red varietal here. An outdoor pizza oven has recently arrived, guaranteeing more alfresco adventures.
3 p.m. Check into the Hampton Inn & Suites, freshly remodeled and located centrally in Windsor. You are walking distance to grocery stores, pharmacies, and eateries directly across the street.
The Hampton Inn is the most comfortable lodging option near downtown. Among the 116 rooms and suites to choose from, I highly recommend booking a suite, terrific for spreading out. The open living room and bedroom concept also features a compact entryway with a microwave and refrigerator, and a separate sink, ideal for keeping snacks or warming up meals. I typically ask hotel staff to bring these items in anyway.
This Hilton property provides all-day coffee and tea, plus complimentary breakfast with fresh fruit, oatmeal, pastries, yogurt, cereal, hot egg and meat entrees, as well as make-your-own waffles. It is a solid breakfast providing the calories to conquer the day. Plus, with the 6 a.m. to 10 a.m. timeframe, you can eat early and come again for your waffles a few hours later. Do laps in the pool or simmer in the hot tub. If you want to plan an all-day pool day, you can comfortably do so under umbrellas on loungers. The lobby has snacks and wine for purchase, so you can chill out without using your car.
And if you want to attempt a no-car vacation, book the Hampton Inn’s SMART Train sails-and-rails bundle. Start in San Francisco by taking the ferry to quaint Larkspur. In Larkspur, board the new SMART train, which ends in downtown Windsor. Walk 15 minutes to the hotel. Windsor: The SMART Way package also provides a couple of $15 Uber vouchers, so you can venture further out during your stay.
6 p.m. Dine in style at Sweet T’s, only a four-minute walk from the hotel. The trendy, yet elegant establishment delivers on Southern comfort foods with elevated cocktails, barbecue meats, grilled entrees, and tons of side dishes and salads. The two-sided menu will make you immediately salivate. My favorite? The combination BBQ platter with fall-off-the-bone pork ribs, brisket, and tri-tip. The house barbecue sauce is too addictive.
8 p.m. Hot tub time. Press that bubble button, and say “ahh” to the spa. Soak under the skies. Don’t come late and get locked out like I did. The Hampton closes the pool gate by 9 p.m. Now you know.
DAY TWO
8 a.m. Pickleball at Hiram Lewis Park. When we found out about the new courts, we immediately packed our racquets. Unlike our city, these pickleball sanctuaries are not packed in the morning, and you can have a court to yourselves. Don’t be surprised if you get invited to a pickup game. We were walloped by residents Leah and Bill, by the way.
10 a.m. Crawl downtown. The Windsor Town Green anchors the downtown core. From the park, boutiques, wine rooms, and restaurants radiate outwards. Need a new outfit? Another jewelry bauble? Shop Roost General Store, a tasteful retailer featuring women’s clothing, home décor, and kitchen goods. Steps away, Mark Shimizu Jewelers is kind enough to offer free jewelry cleaning. Mark’s son works there and has learned the ropes. While waiting, peruse the display of exquisite custom rings, necklaces, bracelets, and earrings.
Windsor’s 19th-century architecture is well preserved, along with buildings that replicate the era. This zone is also home to wine rooms, each with its own spin. On Mondays, jump into a mah-jong game at Mutt Lynch Winery, which offers limited batch wines from small makers. The poster says the game is offered through the summer, but word on the street is that tiles are still being tossed.
12 p.m. Lunch at Pizzaleah. In a nondescript strip mall lies Windsor’s most amazing pizza. Ask neighbors about Pizzaleah, and smiles erupt. Leah, the owner and founder, creates square and round thin-crust pies with wacky, but tantalizing combos. Leah tells us that the most popular is Old Grey Beard with hot honey, orange zest, and Calabrian peppers for a zippy kick.
1:30 p.m. Old vine zin wine tasting. Limerick Lane Winery is, yes, on Limerick Lane. On a spicy fall day, shade yourself under orange umbrellas and dive into the zinfandels it is known for. Tasting room manager Andy pours as he waxes poetic about the property’s dynamic history, which definitely should be a Netflix film.
Inside, window seats yield to crimson, yellow, and pumpkin orange views of undulating vineyards. In winter, you can sit outside under a gazebo and toast to the views while keeping warm. Bringing your own picnic while tasting is fine. Kids and dogs are welcome, too. For future reference, you can rent one of the houses on the property and swim in the pool that’s shaped like a wine bottle.
3 p.m. Ice cream time. Simply Scooped, near Pizzaleah, nails it when you just need an afternoon pick-me-up. The day we arrived as the only customers, our server was happy to provide taste upon taste without getting annoyed. Simply Scooped also offers a myriad of toppings (nuts, cereals, candy, cookies). Ice cream is organic and made in-house with non-dairy picks as well. My recommendation: passion fruit sorbet (vegan), paired with dark chocolate peanut butter. It just works.
3:30 p.m. Mural tour. The walk-it-yourself mural tour will acquaint you with local artists. Pick up a map at the Visitors Center.
Snap a selfie with the Charlie Brown and Snoopy sculptures, and hunt for modern and traditional public art.
6 p.m. Dinner… again! So many restaurants, so little time! Windsor has no lack of international cuisine. However, if you are in the mood for a burger and fries, we’ve got the place for you.
On the other side of town, the Beverage District is drawing beer and spirits lovers. Already iconic is the Russian River Brewing Company which built an 85,000-square-foot, multi-building campus in 2018. It contains the brewing operation, a restaurant, a gift shop, an event space, and a patio. Go on a self-guided tour before you have dinner, and learn all about hops and yeasts that turn water into beer. The menu highlights beer-infused sauces and batters for things like its rock cod fish tacos and ricotta dessert donuts. Unique is its non-alcoholic hop water, which is just that – water that is left over from the hops used for brewing. Try products fermented in aged wine barrels. The Intinction beer is made with petite syrah grapes added in the final phase. Crazy, right?
DAY THREE
8 a.m. Hike Armstrong Redwoods. Less than an hour away, towering redwoods inspire awe. Tackle sweat-inducing trail elevations or play it safe at ground level. Friends took us up a steep climb where the payoff was being able to stand above the clouds.
You don’t have to go as far to experience nature. Chef Buttercup from Windsor’s Fleur Sauvage Chocolates says that minutes from downtown, he mountain bikes the community and regional parks, finding new trails all the time.
11 a.m. Depart hotel. Grab an early lunch at Oliver’s Market. Residents brag about Oliver’s, the employee-owned cornucopia of gourmet provisions and local foods.
Oliver’s is so recognized in Sonoma County circles that it successfully brands its own spices, beverages, sauces, and more. You will swoon over the deli, coffee bar, wine and beer lounge, bakery, taqueria, soup and salad bar, sushi stall, and to-go hot dishes. A must, must, must visit!
12 noon: Chocolate tasting. Handmade chocolate from an award-winning chocolatier doesn’t get any better than this at Fleur Sauvage Chocolates. The shop, fashioned in country French chíc, invites customers to linger inside or outside in its backyard garden. Owners Chef Buttercup (aka Robert Nieto) and wife Tara work hard to please five days a week. Select from an artistic tableau of French desserts, chocolates, coffees, teas, and cold drinks. Also of note: the French-styled hot chocolate receives consistent rave reviews.
The day we came, the chocolate bonbon tasting of four treats and a French press coffee was the way to go. On seasonal weekends, guests can partake in an exquisite afternoon tea. Around the holidays, regulars vie for Fleur Sauvage chocolate Advent calendars.
1 p.m. Sip at Santa Rosa’s Martin Ray Vineyards & Winery, fifteen minutes from Windsor. The bucolic site includes plenty of under-eaves seating, a year-round garden path, and a sky-high water tank emblazoned with its name that’s seen from far away.
Find out when they offer wood-fired pizza, as it is available on a pop-up basis. Secure the secret outdoor table inside the shape of a giant curved wine barrel. Walls are made of repurposed barrel slats.
Do ask for a sip of the fizzy rosè, and explore the complex lineup of pinot noirs and cabs. Request Marty Paradise to pour for you. With decades of experience in the food and wine industry, Marty has many stories and tells them well.
After the trip, you’ll be surprised by how many adventures, conversations, and new friends you’ve made in a short amount of time. At less than eight square miles, Windsor may be small, but its businesses and people possess big hearts.
- Want to explore Windsor on your own? Visit Discover Windsor
