There’s a sense of discovery travelers feel “stumbling” upon a small town. This, of course, is often the evolution of tourism for many destinations, where the quaint can become contrived for the sake of commerce. But there’s plenty of places where both realities can exist.
I grew up in Los Olivos in the Santa Ynez Valley. At that point it was just a little town with a flagpole and a grange hall. A popular annual event called Los Olivos Day in the Country—now in its 45th year—brought people out for pie contests (family lore says that my dad was the first pie contest winner in the late 1970’s) and a parade. But aside from that, it was a very sleepy place.
Flash forward to today, where you can't walk five feet without hitting a tasting room or luxe boutique. Some of that has to do with the movie Sideways, which had a weirdly hefty influence on this whole area after filming here. It’s a fun place to visit, and a lovely place to live, continuing to evolve with plenty to draw visitors and residents alike. Here’s a modern guide to getting around.
Where to Stay in Los Olivos
The Inn at Mattei's Tavern, Auberge Collection
(Courtesy of Inn at Mattei's Tavern, Auberge Collection
Fess Parker Wine Country Inn
This 19-room boutique property is quintessential Los Olivos, originally operating as The Grand Hotel, then purchased in 1998 by actor Fess Parker (famous for playing Davy Crockett and Daniel Boone in the 1950s), whose family still runs it today. The rooms could be out of a Wine Country design magazine, with plush bedding and luxurious ranch-inspired touches. It is in a central location that’s great for walking around town, with plenty of serene private outdoor areas to unwind after a long day of being out and about. A generous European-style continental breakfast is included, served in a sunny side room. // 2860 Grand Ave, fessparker.com/inns-and-cabins/our-inn
The Inn at Mattei’s Tavern, Auberge Collection
This new iteration of a very historic property was a big deal when Auberge Resorts Collection announced the development would open February 2023. Mattei’s Tavern was originally a stagecoach stop in the 1800’s and has been a local landmark ever since, with volumes of thick guestbooks capturing the signatures of visitors from the past. It feels like walking back in time and Auberge took on the renovations and redesign carefully, preserving the details that make it so unique, sloping floors and all. Fitting for the brand, the 67 guest rooms are luxurious and classy, with a simple modern farmhouse aesthetic. Meandering outdoor landscaping, a pool with an outdoor bar, firepits, a wooden water tower, old growth palm trees, and a signature spa (in partnership with Jenni Kane’s Oak Essentials) complete the experience here—and might distract you from the stories that it’s haunted. // 2350 Railway Ave., aubergeresorts.com/matteistavern
Where to Eat & Drink in Los Olivos
Bar Le Côte
(Courtesy of Craft & Cluster/Visit the Santa Ynez Valley)
Bar Le Côte
Similar to how locals view this area pre-Sideways and post-Sideways, it could be said that there is a pre- and a post-Daisy and Greg Ryan. The restaurant scene in the whole Santa Ynez Valley is a lot more delicious in the post-reality, and Bar Le Côte is their Los Olivos gem. Launched in 2021 by the couple behind Michelin-starred Bell’s Los Alamos, Bar Le Côte is inspired by the daily catch of the Central Coast, yet gives big Spanish vibes in both food and energy. It is an incredible addition to LO, in a beloved historic building that was once a pulse point for the town called Side Street Cafe. Ambiance is spot on, warm and inviting, calming yet buzzy and super hip. There are glowing lights, emerald green and terra cotta accents, and bold artwork. A signature dish since day one has been the day boat scallop crudo with pickled mushrooms and dill pollen—but really, you can’t go wrong with anything on the menu. // 2375 Alamo Pintado Ave., barlecote.com
Los Olivos Wine Merchant & Cafe
If we are talking pre-Sideways, then folks will mention Los Olivos Cafe, which was once Clausen’s Old Fashion Deli, where giant pickles were a cheap after school snack. Walking in, you might recognize the space, although it has been spiffed up a bit, from the scene when Miles gets wasted and famously refuses to drink merlot. Today the place is known as Los Olivos Wine Merchant & Cafe, an intentional move by owners Shawnda and Sam Marmorstein who wanted everyone to know that half the space is a wine shop fully stocked with an amazing selection of local producers including their own Bernat Wines label. Produce from their three-acre organic farm just about a mile away is featured prominently on the Mediterranean-inspired menu. This isn’t just a sprig of rosemary in your cocktail from the garden box out back. They really walk the walk—and any extra produce goes to Veggie Rescue, a local non profit. Order off the specials menu for the freshest harvest, but the regular menu highlights the seasons as well, with signature items like the housemade gnocchi with rotating ingredients, like fresh pesto and roasted tomatoes in the late summer. // 2879 Grand Ave., winemerchantcafe.com
Nella Kitchen & Bar
Located in the Fess Parker Wine Country Inn is Nella Kitchen & Bar, with a lovely outdoor patio that is a great place for people watching. From the team behind the very popular S.Y. Kitchen, Nella is Italian-inspired, featuring a wide selection of pinsas (Roman pizza). Plus, this is one of only two bars in town serving cocktails—and they’re great. Try the Barrel-Aged Boulevardier with private label bourbon, Aperol, Thai chocolate cordial, and Cynar. The indoor bar is fun during their “grand hour” or come at night when the rest of the town goes to sleep. // 2860 Grand Ave., nellakitchen.com
The Tavern at the Inn at Mettei’s Tavern
When Auberge Resorts took over this historic train stop known as Mattei’s Tavern, locals held their breath. It’s a big move, and the 139-year-old space has big shoes to fill. The main restaurant here is simply called The Tavern, and executive chef Joseph Humphrey has massaged the California ranch-inspired menu to reflect seasonality and local ingredients, with reverence to some unfussy roots. Cauliflower gets tahini, almond dukkah, spiced local honey, and Fresno chiles, and the summertime salmon special was served crispy skinned with fried Thai basil, lemon verbena, and corn pudding. Adding on Santa Barbara uni for $10 is a no-brainer. And anyone in the know will be happy about the mud pie on the dessert menu, a firm nod to the legacy of this kitchen. A fittingly exceptional wine program is a definitive draw here, while the dim lounge in front serves elevated cocktails. All the spaces have been preserved and refreshed with details like mini gas lamps on each table and dark green leather banquettes. In the morning there’s a little coffee shop tucked away inside the tavern, dark and old fashioned with modern things like a La Marzocco espresso machine, Handlebar coffee, and housemade croissants and syrups. On the side though, you’ll find a cheery and sunny enclosed porch space, great for breakfast lounging. // 2350 Railway Ave., aubergeresorts.com/matteistavern
Lefty's Coffee Co.
Located in a former house on a small side street, Lefty’s is a great addition to the community, with a big dose of mission-driven, activist goals. The certified B Corp has a bunch of cool details aside from just being a cool coffee shop. They have a book store shelf, farm stand with goods from the owner’s farm, Honeybear, and even a free printed Gazette. There’s a full espresso menu plus food, with favorites like a cheesy soft pretzel stick. A large, terraced back patio space is shaded and perfect for lingering or working. // 2896 San Marcos Ave., Lefty's Coffee Co.,
The Other Room
A stone’s throw from Bar Le Côte is an example of the pioneering prowess and collaborative vitality of The Ryan’s Companion Hospitality. This new tiny wine and beer bar is a joint project with Valley Brewers and the BackRoom in nearby Solvang. Crafty brews from area breweries like SLO’s There Does Not Exist, snacks, and an interesting curation of wines by the glass make for a refreshing departure from what you may be drinking the rest of the day. If you just want to pick up a four pack or a bottle, they have you covered. // 2446 Alamo Pintado Avenue, Ste. C, theotherroomlosolivos.com
Bob’s Well Bread
While it’s technically not in Los Olivos, Bob’s deserves a mention here as it’s so close. Over in Ballard, just two miles away, is the second location of Bob’s Well Bread. The first was founded by Jane and Bob Oswaks (former president of worldwide marketing for Sony Pictures) in Los Alamos. His baking hobby turned into a business which quickly became everyone’s favorite, visitors and locals alike. The Ballard shop opened in 2019 and features the same excellent breads, laminated pastries, bagels, cookies, and giant sourdough English muffins—plus a whole menu of breakfast and lunch items. // 2449 Baseline Ave. (Ballard), bobswellbread.com
What to Do in Downtown Los Olivos
Story of Soil
(Courtesy of Craft & Cluster/Visit the Santa Ynez Valley)
Wine dominates the what-to-do question here, although there are still other fun things to be discovered. The first choice for the day is if you will be staying “in town,” meaning the four block quadrant that is downtown Los Olivos, or if you will be exploring the surrounding rural region just outside.
What happens when neighborhoods are zoned residential-commercial is cute houses become cute businesses, giving a town a quaint village feel. Los Olivos’ main street, Grand Avenue, is lined with tasting rooms (home to more than 30), galleries, and boutiques inside Victorian-style buildings. Visit J. Woeste (2356 Alamo Pintado Ave.), Los Olivos General Store (2900 Grand Ave.), Global Eye (owned by ceramicist Kristen Cramer who also has her goods on offer; 2935 Grand Ave.) and the new Wylde West Wreckerds (2933 Grand Ave., Ste. D & E) tucked away upstairs.
It’s almost impossible to list all the tasting rooms you can choose from, so here are just a few.
Story of Soil
Located in a side clump of town set apart from the main strip, owner and winemaker Jessica Gasca started Story of Soil with only three wines in 2012 and a philosophy focused on small-lot, single vineyard, single varietal wines. Her premise is that each wine is a journey that starts in the soil and ends in the bottle (hence the brand’s name). Try the sauvignon blanc, which, interestingly, was harvested in the morning and the afternoon from the same block, two weeks apart, then fermented separately and combined—a unique approach with a big impact. // 2362 Alamo Pintado Ave., storyofsoilwine.com
Gainey Vineyard-Evan’s Ranch
The Gainey label is a longstanding one with a wide reach, exemplifying how diverse the Santa Ynez Valley winegrowing region is. Their Home Ranch is on the eastern side of the Valley, a warmer climate where Bordeaux varieties grow well. In 1997 Dan Gainey bought a cool climate property in the Santa Rita Hills, just 10 miles from the ocean, to get in the pinot noir, chardonnay and syrah game. They named this estate property Evan’s Ranch after Dan’s great grandfather. The Evan’s Ranch tasting room, at a prime location kitty corner to the central flagpole in downtown Los Olivos, features the six limited-productions wines from Evan’s Ranch, which you can taste here without having to drive all the way out to the Santa Rita Hills (although you should at some point, because it’s gorgeous). // 2901 Grand Ave., gaineyvineyard.com
Terre et Sang
This newish tasting room in another former residence, on the northern side of Grand Ave. is where you will learn about mother-and-son team Dalita and Duncan Harmon. They founded the label in 2019, and quickly got on the map with high scores for the 2020 Kissing Vipers Bien Nacido Grenache. Duncan is completely self-taught, leaving his degree from Penn State aside to focus on a love and appreciation of wine imprinted by his mom early on. The label focuses on small-lot syrah and grenache from the best site-driven vineyards of Santa Barbara County. // 2982 Grand Ave., terreetsang.com
A Few More…
The “urban” tasting room trail in downtown is vast, so here are a few more worth ducking into for a taste. Solminer (woman-run natural winemaker; 2890 Grand Ave.), Holus Bolus & The Joy Fantastic (2902 San Marcos Ave., Unit B.), Liquid Farm (winemaker James Sparks also has his own label, Kings Carey, that is excellent; 2445 Alamo Pintado Ave.), Dragonette Cellars (2445 Alamo Pintado Ave.), Stolpman Vineyards (2434 Alamo Pintado Ave.), Future Perfect Wine (2933 San Marcos Ave. #101), and Carhartt Family Wines (2939 Grand Ave.).
What to Do Outside of Downtown Los Olivos
Demetria Estate & Vineyards
(Courtesy of Craft & Cluster/Visit the Santa Ynez Valley)
You won’t regret it hitting the scenic country roads that surround Los Olivos. Driving through rolling golden hills studded with Valley Oaks and the Los Padres National Forest mountains beyond stopping at vineyards and farms along the way is a beautiful way to spend the day.
Olive & Lavender Farms
This charming olive grove and lavender farm at the famous Lansing’s Crossing stagecoach stop is close to town (a great option for a bike ride) but feels like a complete escape. A trio of new co-owners recently purchased the property and added the lavender element, as well as events, an eye for design, and two refurbished Airstreams, one of which is a music studio and soon-to-launch public radio station. The whole gorgeous property feels like a park, with garden boxes and fruit trees and a bocce ball court, and they encourage families and pets to linger. Complimentary tastings of their eight organic olive oils, milled nearby in Happy Canyon, are available by reservation, and there’s a charming shop onsite. They also host a variety of pop ups, like the recent Verto’s Donut and Matcha cart up from L.A. // 2450 Alamo Pintado Rd., oliveandlavenderfarms.com
Roblar Winery & Vineyards
Just up the hill is Roblar Winery, an oak tree-studded 40-acre estate vineyard on the border of Los Olivos and Santa Ynez, with a wide range of wines on offer. They also have a full-service kitchen, where chef Terri Buzzard creates dishes using some of the produce grown onsite and sold at their farmstand. A large back outdoor patio is a lovely spot to enjoy brunch or lunch while sipping a flight. The hummus order is a win, featuring warm homemade pita bread. // 3010 Roblar Ave., roblarwinery.com
Foxen Canyon Road
This is a main wine tasting route and it's worthy of a few stops. The drive is beautiful, and the wine is great, all just a few minutes from downtown Los Olivos. If you are staying at the Fess Parker Wine Country Inn, you’ll get a free tasting at their eponymous Fess Parker Winery & Vineyard on this road, a lovely estate that is perfect for a picnic. The brand, still family owned by actor Fess Parker’s descendants, has been one of the driving labels here. // 6200 Foxen Canyon Rd., fessparker.com
About 10 minutes further along Foxen Canyon is Demetria Winery & Vineyard, a 200-acre biodynamic property growing 35 blocks of wine grapes (mostly Rhone varietals) founded in 2005 by John Zahoudanis, who grew up in Greece in a family that cultivated olives, citrus, and wine grapes. Winemaker Ryan Roark (also has his own label, Roark Wine Company) works in tandem with winemaker and operations manager Emily Myers. A flock of sheep graze the steep, rocky, and windy topography. Tastings are by appointment only. You can book a tour as well, in which Ryan or Emily will take you around the property on an ATV, followed by a cellar tasting and a charcuterie board. // 6701 Foxen Canyon Rd., demetriaestate.com
Hike the Hills
Drive out Figueroa Mountain Road for a glimpse of Michael Jackson’s former Neverland Ranch, then continue towards the majestic Grass Mountain (5100 Figueroa Mtn Rd., Santa Ynez). The hike to the top is steep and challenging, but if you aren’t up for the full adventure, this countryside is still a worthy spot to walk around for a bit.
