Healdsburg: 4 Itineriaries for Any Traveler

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Healdsburg is full of unique restaurants, shops, parks, historical sites, and wineries. With such an eclectic mix of things to do, it’s no wonder that this progressive little town has become a hotspot for travelers of all stripes. The foodie allure is just the start in Healdsburg: couples come here for the town’s romantic charm, and outdoor enthusiasts flock year-round to use it as a base camp for some fun activities that lay just closeby. We’ve put together a customized guide here, so scroll on through until you find your type, and have at it.

For the Outdoors Enthusiast

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Image Source: Yelp

Where to Stay

The Best Western Dry Creek is a more-than-suitable base camp for an outdoor vacation. The hotel sits right at the mouth of Dry Creek Valley, which is a great spot for biking and hiking all by itself. There’s also an outside area with cozy fire pits which provide a nice place to sit and relax while your cool your heels at the end of the day.

Where to get Breakfast

In the morning, head to Big John’s Market for breakfast. This market specializes in seasonal and local groceries, as well as hand-picked imported foods. Plus they’ve got a great onsite bakery, which they adapt for some fresh homemade sandwiches. While you’re there, be sure to pick up a few snacks for your bicycle adventure.

What to do in the Morning

Spend the morning riding through Dry Creek Valley on West Dry Creek Road. This lovely thoroughfare will take you over rolling hills and past numerous wineries, including Comstock Wines, Wilson Winery, and Mauritson Wines. If you’d like, stop in for a tasting or tour.

Where to get Lunch

For lunch, head to the Dry Creek General Store. This historic general store offers farm-fresh food, including hand-crafted sandwiches, salads, and soups. After you’ve bought your food, head outside to Dry Creek General Store’s lush garden and have a picnic.

What to do in the Afternoon

In the afternoon, bike over to Dry Creek Vineyard and sign up for the Bocce in the Vineyard wine tasting experience. You’ll be given your own bocce court for two hours, as well as a bottle of Chenin Blanc or Fume Blanc to enjoy while you play. There are snacks available for purchase from Dry Creek Vineyard’s tasting room, too.

Where to get Dinner

For dinner, head back to downtown Healdsburg and check out the Wurst Restaurant. This casual eatery offers delicious sausage, bratwurst, and burgers, and they have a hefty list of craft beers and local wines, to boot. Ask to be seated on their lovely patio.

What to do for Nightlife

Take a drive out to Medlock Ames Vineyards. The journey will take you through the beautiful countryside surrounding Healdsburg, but once you arrive at Medlock Ames, head to the Alexander Valley Bar, located behind their tasting room: this chic bar is set up like a speakeasy, and offers artisanal cocktails, local wines, and microbrews.

Insider tip: If you need to rent a bike, head to Wine Country Bikes, where you can nail down some wheels for seven days. Make sure to ask for a bike route map from their shop, too—they know where all the bikeable surprises are.

For the Foodie

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Image Source: Yelp

Where to Stay

Base yourself at Hotel Les Mars during your food tour of Healdsburg. The luxurious French-style hotel is located downtown, and is within walking distance from many of Healdsburg’s top restaurants. They also have a highly rated on-site restaurant, Chalkboard.

Where to get Breakfast

Walk over to the Healdsburg SHED Café, located right next door to Hotel Le Mars. This eatery is housed in a modern, airy room with large windows, and boasts a menu that changes daily, while still always featuring seasonal and fresh ingredients from local farmers.

What to do in the Morning

A blending class at Hawley Winery is a great way to spend a morning. This two-hour class is held from 10 am to 12 pm in Hawley’s cellar, and teaches guests the basics, nuances, and finer points of blending wine. Reservations are required.

Where to get Lunch

Relish Culinary Center touts some of the area’s most popular culinary classes: one of the most-so is the farmers market-to-pizza workshop. During this class, you’ll shop for ingredients in the local farmer’s market, bring them back to your workstation, and will be taught the fine art of creating your own pie.

What to do in the Afternoon

Sample some small bites and wine pairings at the Siduri Tasting Lounge, a modern venue where you can try some of Siduri’s most popular Pinot Noirs, paired with small plates from their on-site chef. For the adventurous, customizing a tasting is totally doable—just ask.

Where to get Dinner

For dinner, head back to Hotel Les Mars and dine at the Chalkboard Restaurant. This casual and contemporary eatery serves homemade pasta and small plates that highlight seasonal ingredients, with many of the vegetables and herbs harvested straight from Chalkboard’s private, three-acre garden.

What do for Nightlife

End your night with dessert at Mustache Bakery, and opt for a cupcake made with seasonal ingredients. This popular shop also offers delicious French macaroons, and ice cream sandwiches that have become famous.

Insider tip: On Tuesdays and Wednesdays from May to November, the Healdsburg Farmers Market takes place downtown. Stop by and pick up locally grown watermelon, apples, berries, and more—whatever’s in season.

For the Romantic

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Image Source: Yelp

Where to Stay

For your couple’s getaway to Healdsburg, stay at the Camellia Inn. This peaceful inn has nine rooms that feature an eclectic mix of antique furnishings and modern fixtures, and the property is conveniently located walking distance from the downtown plaza.

Where to get Breakfast

For breakfast, take a trip to one of the most romantic eateries in Healdsburg, the Costeaux Café. You’ll feel like you’ve been transported to Paris while you sit in the chic space and munch on quiche, pain perdu, freshly baked croissants, and other French delicacies.

What to do in the Morning

Sign up for a couple’s spa package at the Hotel Healdsburg. This blissful combination of services includes a 75-minute side-by-side massage in the couple’s suite, a 25-minute soak in the Jacuzzi, glasses of JCB Sparkling rosé, chocolate truffles from Dry Creek Kitchen, and day use of all spa facilities (in case you decide to stick around for a while).

Where to get Lunch

Grab a tandem bike at Spoke Folk Cyclery, and head on over to Oakville Grocery, where you’ll find gourmet sandwiches, some snacks, and a selection of local wines. Then, take your picnic outside to their patio, and enjoy a leisurely lunch in the sunshine.

What to do in the Afternoon

Spend your afternoon enjoying a wine and chocolate tasting at Season’s of the Vineyard, which touts five Ferrari-Cerrao wines paired with Scharffen Berger chocolates. The tasting takes place in Season’s of the Vineyard’s tasting bar in their boutique gift shop.

Where to get Dinner

Scopa Italian Bistro is a small, rustic restaurant that’s just ideal for a date night. They have an extensive wine list with both local Napa Valley and Italian wines, and their kitchen has become a popular spot for authentic Italian pizza, homemade pastas, and seafood dishes.

What to do for Nightlife

End the day with a few drinks and dessert at Spoonbar, which offers classic, original cocktails that use organic and local herbs, as well as local spirits. The bar is small and intimate, with gorgeous windows that offer an amazing view of town.

Insider tip: At Spoonbar, get a s’mores dessert to share: this tasty sweet features cinnamon meringue, chocolate ganache, salted bourbon ice cream, and homemade graham cracker crumble.

For the Urban Adventurer

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Image Source: Yelp

Where to Stay

Unpack your bags at Healdsburg Inn on the Plaza. This stylish and historic B&B was built in 1901, and it features twelve spacious guestrooms with fireplaces and modern décor, but it’s especially popular for its prime location downtown, which makes exploring the town on foot a breeze.

Where to get Breakfast

The bright yellow Parish Café serves Cajun and Creole specialties, including a breakfast po’ boy, a crawfish and andouille omelet, shrimp and grits, and powdered beignets.

What to do in the Morning

Opt for some shopping downtown. If you’re interested in antiques, check out Mill Street Antiques, which is packed with vintage furniture, signs, kitchenware, and more. Or, if you’re looking for gifts or clothing, try some boutique shops, like Bella, Zizi, or Yasuko.

Where to get Lunch

Mateo’s Cocina Latina serves inventive Yucatan dishes in a modern atmosphere, and also boasts a tequila bar filled with imported bottles. If it’s nice outside, ask to be seated on their garden patio.

What to do in the Afternoon

Wine tasting is a pastime in this part of California, and it’s no different in downtown Healdsburg. Start by going to the La Crema tasting room, a contemporary lounge-style room that offers limited-edition bottles direct from the La Crema Winery. Also, be sure to spend some time at the hip Spicy Vines tasting room—this stylish venue features work by local artists, and has myriad wines available for sale (for something a little different, try one of their wine cocktails).

Where to get Dinner

BarnDiva’s motto is: “wherever you are, eat the view,” and once you see this restaurant’s interior, you’ll understand why. The restaurant serves modern Southern cuisine in a restaurant styled to look like a barn. Their menu changes with the season, so they are always able to serve the freshest food possible.

What to do for Nightlife

Finish your day in downtown Healdsburg at Duke’s Spirited Cocktails. The upscale lounge offers locally inspired cocktails as well as local wines and beers, so grab your drink, sit back, and toast to a wonderful day in Healdsburg.

Insider tip: If you’d like a little champagne with your shopping, check out Looking Glass boutique. This shop has designer clothing and an on-site lounge that serves specialized champagne and sparkling wine.

While this town has achieved some fame because of its inventive food scene, the culinary offerings just scratch the surface. Outdoor adventures in the sun, some one-of-a-kind shopping experiences, and a few unexpected surprises are only a few things the casual visitor can expect during a trip to this delightful neck of the woods.