Did you know that Santa Cruz County has the fifth-largest population of artists per capita in the United States? The community is brimming with talented artists who make a lively and colorful mark on the county. And when it comes to wine, the Santa Cruz Mountain AVA – one of the oldest wine regions in the country – has more than 70 wineries and 200 growers. Pairing art and wine is a summer favorite in Santa Cruz County and these festivals will give you a unique taste of what the area has to offer. Prefer beer over wine? There are some great opportunities to enjoy some local brews as well! Get out your calendar and start planning for this Summer’s Art, Wine (and Sometimes Beer) Festivals and Events in Santa Cruz County!
Various 2026 Dates
Vine to View Farm to Table Wine Dinners at Chaminade Resort
From Vine to View Overlooking Santa Cruz & Monterey Bay. Locally sourced and perfectly paired, Chaminade’s Vine to View Dinners are back with an exciting line up for 2025! Join Chaminade Resort as Executive Chef Samuels and his culinary team create gourmet five-course dinners expertly paired with wines from local California vineyards. See dates below and visit their website for tickets and menu details.
- Friday, Mau 1 with Beauregard Vineyards
- Friday, June 5 with Caymus Vineyards
- Friday, July 10 with Wente Vineyards
- Friday, July 24 with Storrs Winery
- Friday, August 7 with Fableist Wine Co.
- Friday, September 11 with Serial Wines
Various 2026 Dates
NICHOLSON VINEYARDS: SUMMER SERIES
Enjoy summer weekend afternoons at the beautiful Nicholson Vineyards! Bring along a picnic and Sip delicious wines in the Corralitos countryside with various vendors and music throughout the season! Saturdays & Sundays from 1pm to 4pm.
- July 11 & 12: The Clay Chalet and music by Dos Bros
- July 18 & 19: Indigo and Vine and music by Jo Coleman
- July 25 & 26: Sour Sammy Sourdough and music by Six String Mixtape
- August 1 & 2: Scout and Sea and music by Half Pass
- August 8 & 9: Lili Arnold Studios and music by Eden Edell
- August 15 & 16: Desert Moon Design and music by Kip Allert
- August 22 & 23: Papelline Jewelry and music by Zach Bailey
- August 29 & 30: Anna Gail Designs and music by Jeff Smith
- September 5 & 6: All You Knead and music by Cake Party!
Various 2026 Dates
LESTER ESTATE WINES: SUMMER SUNDOWNER CONCERTS
Live music, food and wine overlooking the Lester Family Vineyards in the heart of Pleasant Valley.
- Friday, June 12 from 5-8pm: Music by Alex Lucero Band and Food by SnB Food Truck
- Friday, July 3 from 5-8pm: Music by B-Movie Kings and Food by Happy Dog
- Friday, July 10 from 5-8pm: Music by Bastard Sons of Johnny Cash and Food by Uncle Papa’s BBQ
- Friday, August 14 from 5-8pm: Music by Nautical Thrust and Food by Italia Fire
- Friday, September 18 from 5-8pm: Music by James Durbin & The Lost Boys and Food by SC Eatery
- Sunday, October 4 from 3-6pm: Music by Jive Machine and Food by High End Comida
Various 2026 Dates
ROBERTS RANCH VINEYARDS: WINE & DEJEUNER d’OUVIER
This year, Roberts Ranch Vineyards is celebrating the French Provençal communal tradition of the Déjeuner d’Ouvrier, also known as the Worker‘s Lunch. This is a perfect time to grab some friends and gather around the table for a generous prix fixe communal lunch of delicious soup and main course, artisan bread, a fruit and cheese course salad and (bien sur) dessert! One Saturday each month from 11:30am to 1pm. The menu will be published on Eventbrite two weeks ahead of the event date.
- Saturday, August 8
- Saturday, September 5
Various 2026 Dates
ROBERTS RANCH VINEYARDS: WINE TASTING AND CRUSHPAD CONCERT
Enjoy a tasting of 5 of the current Roberts Ranch wines complete with abundant charcuterie boards! Meats, cheeses, crackers, nuts, fruits, chocolate and even warm appetizers make appearances at this lovely and casual tasting experience. (See Seltzer & Charcuterie option for those not partaking in the wine tasting.) Attended children and well behaved pups are welcome to join. One Saturday each month from 3pm to 5pm. (Except on 4th of July which is 2pm to 4pm.)
- Saturday, June 6: Steve Abrams Jazz Trio
- Saturday, July 4: Dan & Laurel
- Saturday, August 8: Samba Cruz
- Saturday. September 5: Mountain Drive
Various 2026 Dates
LESTER ESTATE WINES: GUIDED HIKE
Enjoy a 90-minute guided hike through the vineyards and ranch. Get your heart pumping as you hear about the wine’s journey from soil to glass. Part education, part exercise, part wine experience with sips and snacks along the way. This is a moderate hike with some small hills. Please note, this experience is not available to those guests who have mobility constraints or require assistance with walking or standing.
- Saturday, June 20
- Saturday, July 25
- Saturday, September 26
May 16, 2026
WATSONVILLE: WINE, BEER, AND ART WALK
The City of Watsonville and the Pajaro Valley Chamber of Commerce and Agriculture are pleased to partner together to present our 5th Annual Wine, Beer and Art Walk in historic downtown Watsonville on Saturday, May 31, 1pm – 5pm. This event is a great way for locals and visitors to experience great local wines, craft beers, delicious food and artwork by talented local artists while they stroll downtown.
May 30 – May 31, 2026
ROARING CAMP: REDWOOD MOUNTAIN FAIRE
Dance the day away to live music with your friends and family while enjoying tasty locally made food, cold beer, cider and wine in an open field surrounded by redwoods in the Santa Cruz Mountains. There will be three stages of musicians with Jesse Daniel headlining, and kids activities available.
July 11, 2026
HOP N’ BARLEY BEER FESTIVAL
This family and dog friendly beer festival is celebrating fun in the sun with craft brews from far and wide! From San Diego’s Modern Times Beer to Eureka’s Humboldt Cider, makers from across California will be in attendance. Santa Cruz’s booming craft beverage scene will also be heavily represented by breweries and cideries new and old including: Santa Cruz Mountain Brewing, Discretion, Humble Sea, East Cliff Brewing, Shanty Shack, New Bohemia, Seabright Brewing, Santa Cruz Cider Company, Tanuki Cider, and Soquel Cider. So bring the whole family and enjoy amazing live music, fantastic food, over 50 breweries and so much more!
July 18 – 19, 2026
BARGETTO WINERY ART & WINE FESTIVAL
Enjoy a weekend filled with Art, Wine, and Live Music! Shop over 30+ Local Artists and Food Vendors including jewelry, leather goods, paintings & watercolors, mosaics, photography, textiles, woodworks, candles, succulent arrangements, soaps and body lotions, snacks and other great gifts. Saturday and Sunday, 11am – 5pm; live music: 11:30-4pm. Free Admission; Wine Tasting with Purchase of a Festival Glass.
August 1, 2026
SANTA CRUZ MOUNTAINS BREWGRASS FESTIVAL
Head to Roaring Camp for the Annual Santa Cruz Mountain Brewgrass Festival. The day features local breweries, music from favorite bluegrass artists, and food from popular local food trucks. VIP Brewgrass Tasting Train round-trip from the Santa Cruz Beach Boardwalk to Roaring Camp.
August 15 – 16, 2026
SCOTTS VALLEY ART, WINE AND BEER FESTIVAL
The Scotts Valley Art, Wine and Beer Festival is a summer favorite! They go above and beyond with over 100 artists, award winning wines and beers, live music and entertainment, a Saturday car show, Dog Day Sunday, food trucks, kid zone, and more! Don’t miss this two day event! There are lots of tasting and drink ticket options – see their site for details and pre sale tickets. August 15 & 16, 2026: Saturday, 10am – 6pm; Sunday, 10am – 5pm.
September 6, 2025
BONNY DOON: ART WINE AND BEER FESTIVAL
Go to the 23rd Annual Festival! It’s the best little party in the Santa Cruz Mountains! Participate in an afternoon of tastings with local wineries & breweries, artist and craft vendors, food, music and dancing, wine pull, silent auction and all around good vibes. Non-alcoholic beverages are also available. Must be 21 or older to attend. Free admission. 3pm – 8pm.
September 12 – 13, 2025
43RD ANNUAL CAPITOLA ART & WINE FESTIVAL
Stroll the festival with friends and family, sipping exceptional wines from Santa Cruz Mountain wineries while admiring the artistic talents of over 100 fine artists. Sway to live music and be inspired by local dance groups while taking in the ocean breeze and breathtaking view of the Monterey Bay. Feed your cravings with tantalizing cuisine from local food purveyors, and cruise through the Artisans Marketplace for locally handcrafted goods. If that isn’t enough, Capitola Village is filled with restaurants for every taste and charming boutiques to satisfy a shopper’s dream. Art, wine, music, and gourmet cuisine in the enchanting beach-side setting of Capitola Village…summer’s last hurrah, and truly a weekend in paradise! Saturday 10am – 6pm; Sunday, 10am – 5pm. *No pets allowed
September 27, 2025
TASTE OF SOQUEL FESTIVAL
Taste, sip and tap your toes as you sample local eateries, farms, breweries, vintners and musicians of the Soquel neighborhood! Enjoy kids’ games, prizes and more! Free admission. 11am – 4pm.
Want more summer wine-focused events? Stop by Bargetto Winery for their Thursday Night Music in the Courtyard or set sail on the Chardonnay or O’Neill Yacht Charters for wine over the Monterey Bay. Cheers to great summer events in Santa Cruz County! Plan ahead and book your stay!