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Holiday in Healdsburg

Spend Mother’s Day in this charming small town that boasts big fun.


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Nancy D. Brown

9 a.m.

Saddle up for a leisurely guided horseback ride through Chalk Hill Estate Winery’s 1,300 acres of trails and vineyards. You might find yourself astride one of owner Rafael Hernandez’s polo ponies.He has horses for every riding level. Wet your whistle postride with a complimentary tasting of Chalk Hill’s award-winning wines. Wine Country Trail Rides, (707) 494-0499, vineyardrides.com.
 

11:30 a.m.

Lunch at Jimtown Store. This Sonoma County landmark was featured on Food Network’s Diners, Drive-Ins and Dives. Order the brie and Jimtown chopped olive sandwich, and head to the wisteria-covered back patio. Collectors and cooks: Bring home souvenirs like old-fashioned candy, local foods, and vintage toys. (707) 433-1212, jimtown.com.
 

Nancy D. Brown

1:30 p.m.

Ready for some stellar views and more wine? Grab your camera, and head for White Oak Vineyards and Winery. Don’t miss the whimsical art collection as you climb to the tower for nonstop vineyard views. With its Mediterranean-style winery and palm-tree–studded grounds, photo opportunities abound. Be sure to snap a picture with Mom in front of the dancing fountain. (707) 433-8429, whiteoakwinery.com.
 

3 p.m.

Time for some retail therapy! Head to Healdsburg Plaza to visit indie book stores Copperfield’s and Levin & Company. Foodies should make their way to Powell’s Sweet Shoppe, which often carries Sonoma specialty items such as fresh-pressed olive oils and apple cider syrup. There are 15 tasting rooms within walking distance of the plaza, including family-run Williamson Wines, which offers complimentary food and wine tasting. Upgrade to the private tasting of Bordeaux reds, Cabernet Sauvignon, and Library wines starting at $125. (707) 433-1500, williamsonwines.com/tasting-room.
 

Courtesy of Honor Mansion

4 p.m.

Check in at nearby Honor Mansion for some VIP treatment. Go for a massage in your own poolside cabana, or engage in some friendly competition with croquet, bocce ball, tennis courts, and the PGA putting green. Walk the manicured grounds, admire the vineyards, and by all means, stop and smell the roses. (707) 433-4277, honormansion.com.
 

Cedric Glasier6 p.m.

While there are many dining options on the plaza, for comforting Italian food, you’ll want to make a reservation at the tiny but wildly popular Scopa. Order the ciabatta bread, baked goat cheese salad, and Nonna’s tomato-braised chicken. (707) 433-5282, scopahealds burg.com. Or for more casual Italian, check out Scopa’s dressed-down spin-off, Campo Fina. (707) 395-4640, campo-fina.com.
 

9 p.m.

Still up for some fun? Bergamot Alley pairs microbrews with magic shows and movies. (707) 433-8720, bergamotalley.com. And Healdsburg’s best cocktails are concocted by the mixologists at chic Spoonbar inside the H2Hotel. (707) 433-7222, spoonbar.com.

 

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