Grab your wine glasses and sketch pads because the art & wine festivals 2025 lineup is shaping up to be absolutely spectacular! As someone who’s spent countless weekends wandering through California’s vineyard-adjacent art exhibits with a glass of Cabernet in hand, I’m beyond ready to share this year’s must-visit festivals with you. The 2025 season promises to combine the best local wines with incredible artistic talent from coast to coast.

Whether you’re a seasoned festival-goer or planning your first art & wine festivals 2025 experience, this guide has everything you need. I’ve mapped out the coolest events where you can sip premium wines while browsing beautiful artwork. And trust me, after attending dozens of these gorgeous gatherings over the years, I know exactly which ones are worth marking on your calendar!

Art and Wine Festival Ticket Links 2025

April 2025

California Wine Festival – Dana Point (April 25-26, 2025)

• Official Website: California Wine Festival
• Buy Tickets: Eventbrite – 2025 California Wine Festival – Dana Point
• Location: Laguna Cliffs Marriott Resort & Spa, Dana Point, California
• Event Details: Friday (April 25) – Sunset Rare & Reserve Tasting 6:30pm-9pm, Saturday (April 26) – Beachside Wine Festival 1pm-4pm (VIPs 12pm)

Wine Spectator’s Grand Tour – Seminole, Florida (April 26, 2025)

• Official Website: Wine Spectator’s Grand Tour
• Buy Tickets: Grand Tour Official Tickets
• Location: Seminole Hard Rock Hotel & Casino, Hollywood, Florida
• Event Details: Features 200 wines rated 90+ points, includes a souvenir wine glass and gourmet food

May 2025

Art and Wine Festival – Downtown Sykesville (May 3, 2025)

• Official Website: Sykesville Main Street
• Buy Tickets: Purchase Tasting Tickets – $50
• Premium Option: “Wine of Mine” Ticket (includes a bottle to go)
• Location: Main Street, Sykesville, Maryland
• Event Details: Unlimited wine tastings, live entertainment, and local artists

Coronado Art & Wine Festival (May 10, 2025)

• Official Website: Coronado Art & Wine Festival
• Buy Tickets: Eventbrite – Coronado Art & Wine Festival 2025
• Location: 10th & C, 1125 10th Street, Coronado, California
• Event Details: General admission is FREE, wine tasting requires a paid ticket

Wine Spectator’s Grand Tour – Chicago (May 10, 2025)

• Official Website: Wine Spectator’s Grand Tour – Chicago
• Buy Tickets: Tixr – Wine Spectator’s Grand Tour Chicago
• Location: Sheraton Grand Chicago Riverwalk, Chicago, Illinois
• Event Details: General Admission (7pm entry) – $250, VIP options available

National Harbor Wine & Food Festival (May 2025 – specific date not listed)

• Official Website: National Harbor Events
• Tickets: Not yet available for 2025, check the website closer to the event date
• Location: National Harbor, Maryland
• Previous Year’s Info: Spring Wine Festival at National Harbor

June 2025

Napa Valley Wine Auction (June 6-7, 2025)

• Official Website: Auction Napa Valley
• Buy Tickets: All-Access Tickets – $5,000 per person
• Location: Napa Valley, California
• Event Details: Includes Napa Valley Barrel Auction, vintner-hosted dinners, and the Live Auction celebration

Aspen Food & Wine Classic (June 20-22, 2025)

• Official Website: Food & Wine Classic in Aspen
• Buy Tickets: Tickets go on sale January 22, 2025
• Location: Aspen, Colorado
• Event Details: America’s premier culinary festival featuring wine tastings and celebrity chefs

Later in the Year

New York City Wine & Food Festival (October 17-20, 2025)

• Official Website: NYC Wine & Food Festival
• Buy Tickets: Tickets not yet available for 2025, usually go on sale in July
• Location: Various venues throughout New York City
• Event Details: Premier culinary celebration featuring top chefs and food personalities

San Diego Bay Wine & Food Festival (November 7-9, 2025)

• Official Website: San Diego Food + Wine Festival
• Buy Tickets: Fast Forward Events – San Diego Food + Wine Festival 2025
• Location: San Diego, California
• Event Details: Grand Tasting event held outdoors on the bay near Seaport Village

Additional Tips

• Some festivals offer early bird pricing, so checking websites regularly is recommended
• VIP options often include early entry, exclusive areas, and premium selections
• Many festivals sell out quickly, particularly the more prestigious ones like Aspen Food & Wine Classic
• Some hotels offer special packages that include festival tickets, such as The Dana on Mission Bay for the San Diego Bay Wine & Food Festival

Spring into Art & Wine Season: April’s Top Festivals

April kicks off the art & wine festivals 2025 calendar with some spectacular events that perfectly capture spring vibes. The weather’s warming up, and so are the festival offerings! These early-season gatherings set the tone for what promises to be an amazing year of cultural experiences paired with perfect pours.

The California Wine Festival in Dana Point (April 14-15) remains one of my absolute favorites. Set against the breathtaking backdrop of the Laguna Cliffs Marriott Resort & Spa, this oceanfront celebration features hundreds of California’s finest wines alongside gourmet appetizers from top-notch local restaurants. I attended last year and spent hours sampling rare vintages while gazing at the Pacific—heaven! The jazz quartet playing in the background created the perfect ambiance for appreciating both the wine and the stunning coastal artwork on display.

Looking for something on the East Coast? Wine Spectator’s Grand Tour hits Seminole, Florida on April 26th. This prestigious event showcases only wines rated 90+ points, making it perfect for those looking to sample truly exceptional vintages. Their signature commemorative wine glasses make fantastic souvenirs, and the expert-led seminars are incredibly informative for both beginners and connoisseurs alike. Wine tourism enthusiasts will appreciate the international selection that lets you “travel” through wine regions without leaving Florida.

May’s Must-Visit Art & Wine Festivals 2025

May brings even more incredible art & wine festivals 2025 as the season truly hits its stride. These spring festivals offer the perfect blend of outdoor enjoyment, artistic expression, and wine exploration, making them ideal for weekend getaways or day trips with friends.

The charming Downtown Sykesville Art and Wine Festival (May 3) transforms Main Street into a vibrant celebration of regional wines and local artists. What makes this Maryland gem special is the unlimited tastings included with your ticket! My girlfriend went last year and couldn’t stop raving about the handcrafted jewelry and pottery she found while sampling wines from small-batch producers. The food truck lineup is always impressive too, with everything from gourmet grilled cheese to artisanal desserts.

Back in California, the Coronado Art & Wine Festival (May 10) offers an island vibe that’s hard to resist. This festival spreads across the picturesque streets of Coronado with artist booths showcasing everything from watercolors to sculpture. The dedicated wine village features some of California’s most respected vineyards, and what I love most is how food and wine pairing opportunities are built right into the experience. Don’t miss the children’s art zone if you’re bringing little ones – they can create their own masterpieces while you sample the grown-up beverages!

Chicago hosts Wine Spectator’s Grand Tour on May 10th as well, featuring some of the world’s most prestigious wines. The expert-led seminars here focus on wine regions and varietals, making it educational and delicious. Meanwhile, the National Harbor Wine & Food Festival in Maryland offers waterfront tastings with stunning views of the Potomac River. The combination of maritime breezes and carefully selected wines creates a truly memorable tasting experience.

June’s Elegant Art & Wine Festival Experiences

June brings some of the most prestigious art & wine festivals 2025 has to offer. These early summer gatherings blend luxury experiences with artistic excellence, creating unforgettable weekends for serious wine and art aficionados.

The legendary Napa Valley Wine Auction (June 6-7) is as much about exclusive access as it is about amazing wine. I was lucky enough to attend in 2023, and the opportunity to bid on rare vintages while mingling with renowned winemakers was incredible. The intimate dinners set in picturesque vineyards feature multi-course meals paired with limited-release wines you simply can’t find elsewhere. Sonoma Valley wine enthusiasts often cross over to Napa for this event because it’s just that special.

For a mountain retreat with world-class wine, the Aspen Food & Wine Classic (June 20-22) combines breathtaking scenery with culinary excellence. This festival attracts celebrity chefs and master sommeliers who lead tastings and demonstrations throughout the weekend. The grand tastings under the massive white tents feature hundreds of wines from around the world, and between sips, you can browse incredible mountain-inspired artwork from local and national artists. The combination of alpine air and fine wine creates a tasting experience like no other!

Fall into Flavor: Autumn’s Top Art & Wine Festivals

The art & wine festivals 2025 calendar extends well beyond summer, with some of the year’s most anticipated events happening in the fall. These autumn gatherings often feature harvest celebrations and seasonal specialties that showcase the best of the year’s vintages.

The New York City Wine & Food Festival (October 17-20) brings a sophisticated urban twist to the traditional wine festival. The night markets feature global cuisines paired with international wines, and the waterfront celebrations offer stunning views of the Manhattan skyline. Art installations throughout the festival grounds create conversation pieces between tastings, and the auction items often include one-of-a-kind artistic creations alongside rare wine collections.

November brings the San Diego Bay Wine & Food Festival (November 7-9), a beachfront celebration that perfectly captures Southern California’s laid-back luxury vibe. I go almost every year, and the sunset tastings are absolutely worth planning your entire trip around. There’s something special about sampling international wines while watching the sun dip below the Pacific horizon. The luxury tastings and chef demonstrations add educational elements to what’s ultimately a feast for all senses. American wine history often takes center stage here, with special sections dedicated to California’s pioneering vineyards.

Making the Most of Your Art & Wine Festival Experience

Having attended countless art & wine festivals 2025 predecessors over the years, I’ve gathered some insider tips to help you maximize your festival experience. A little planning goes a long way toward ensuring you have the best possible time!

First, purchase wine festival tickets 2025 as early as possible—especially for the more prestigious events like Aspen and Napa, which often sell out months in advance. Many festivals offer early bird pricing with significant discounts, and some include VIP packages that provide exclusive access to limited tastings or special artist meet-and-greets.

Consider transportation carefully—most festivals offer shuttle services, which I highly recommend using. Nothing ruins a perfect wine day faster than worrying about driving home! Some festivals partner with nearby hotels to offer wine festival accommodation packages that include transportation to and from the event.

Don’t forget to check each festival’s art festival vendor information before you go. Many artists take commissions on-site or offer shipping for larger pieces. And if you’re particularly fond of a specific winery, inquire about French wine history or other regions that might influence their winemaking style—vintners love talking about their craft and often pour more generously for engaged visitors!

The 2025 festival season promises incredible experiences for wine lovers and art enthusiasts alike. From coastal California to mountain Colorado, charming Maryland to bustling New York, there’s a perfect festival waiting for you and your friends to explore. Which of these amazing art & wine festivals 2025 will you be attending? Grab your calendar and start planning—these unforgettable weekend adventures combining creativity and cabernet are absolutely worth the trip!

Remember to pack your comfy shoes, bring a reusable water bottle (staying hydrated between tastings is crucial!), and leave room in your suitcase for the beautiful art pieces and wine bottles you’ll inevitably want to bring home. Here’s to beautiful art, delicious wine, and the wonderful memories you’ll create at these fantastic festivals!