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Pair craft beer with comfort classics: Start your Windsor visit with a pint of Pliny the Elder at Russian River Brewing Company (or Pliny the Younger, if you are visiting in February). The new 85,000-square-foot facility offers plenty of fun for beer lovers: guided and self-guided tours, a beer-tasting salon, a 1-acre, pet-friendly beer garden, a 195-seat restaurant, and two bars. Your thirst quenched, head to Kin restaurant, a well-loved, family-friendly dining destination on the Town Green serving up comfort food classics.
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With an extensive menu that ranges from burgers and frickles (fried pickles) to braised short ribs and mac and cheese, you’ll have no problem soaking up those Plinys at Kin.
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Rest your head: The Holiday Inn Express Windsor is conveniently located within walking distance from both the Town Green and Russian River Brewing Company. The hotel offers a continental breakfast and an outdoor swimming pool and hot tub for those looking to relax before or after a day on the town.
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Start your day the Windsor way: The Omelet Express is a Sonoma County staple and is consistently named among the best breakfast destinations in the area. Its two locations, one in Santa Rosa and one in Windsor, serve up egg-cellent dishes: order the Eggs Benedict and pair them with a mimosa.
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For a fancier breakfast, head just south of Windsor to the River Vine Cafe at Vintners Inn, another favorite breakfast spot in Sonoma County. The breakfast and brunch menu is sourced from local farmers as well as the inn’s organic gardens. Located on the border of the Russian River Valley, wine tasting experiences are just around the corner. A fan of rose? Head to these wineries.
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Taste the Russian River Valley: North of Windsor, Rodney Strong Vineyards and J Vineyards & Winery share a driveway, which means you can spend some time at two wineries without having to do any driving in between. Book a guided tour of the Rodney Strong Vineyards cellar and taste wine samples straight from the barrels. Afterwards, get pampered in the J Bubble Room (pictured): their five-course wine and food pairing menu features both sparkling and still wines.
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Find a tasting room at the end of the trail: West of Windsor, the Riverfront Regional Park offers views of the Russian River, lakes and vineyards. Redwood trees provide shade over easy walking trails and there are picnic tables, too. After getting your steps in, make your way across the street to Copain Wines. The appointment-only winery, which specializes in vineyard-designated pinot noir, chardonnay, and syrah, is perched on a hillside overlooking the Russian River Valley.
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Have Mexican for lunch: A favorite among locals, El Gallo Negro is a family-owned restaurant serving authentic Oaxacan cuisine, such as mole made with 30 secret ingredients. This isn’t your usual taqueria, but “a funky mezcaleria” featuring juicy cocktails spiked with smoky mezcal and tequila. Share a molcajete with your travel companion(s). The extra-large dish features grilled steak, chicken, and giant prawns sautéed with onions and served with guacamole, salsa fresca, and chipotle sauce.
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Broaden your beer horizons: Considering its relatively small size, Windsor is practically packed with topnotch breweries. In addition to Russian River Brewing Company, there are three more worth a visit: St. Florian’s is named after the patron saint of firefighters and a minimum of 5 percent of all proceeds go to fire-related, community-based causes. The recently-opened No Quarter pairs pints with Healdsburg-made Journeyman Meat Company sausages. Barrel Brothers is popular for its lively taproom where you can bring dogs and children without a problem.
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Make your dinner memorable: After its original location burned down in the 2017 Tubbs fire in Santa Rosa, Sweet T’s Restaurant + Bar made a sweet return in the town of Windsor. Combining southern cuisine with craft cocktails, this is a favorite locals’ hangout. Try their Catfish Po’ Boy, basted in creole mustard and Louisiana hot sauce.
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Fried chicken at Sweet T’s in Windsor.
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Red Headed Mule at Sweet T’s in Windsor.