Table of Contents
Festival
Fiesta del Sol (Solana Beach)
May 31 – June 1, 2025
Sun, sand, and over a dozen bands? Count us in. Fiesta del Sol is basically summer’s way of saying, ‘Let’s party before the sunscreen runs out.’ Plus, where else can you enjoy tacos, tunes, and crafts with a side of ocean breeze?
Vines & Vittles Family Festival
May 31, 2025
Wine, food trucks, a kid’s zone, and live music—finally, a festival where you can sip syrah while your kid zip-lines. Rancho Bernardo’s Vines & Vittles lets you eat, drink, and be charitable, all in a family-friendly setting. It’s basically a backyard barbecue, if your neighbors were gourmet chefs and local vintners.
Valley Center Western Days (75th Annual)
May 30 – June 1, 2025
Giddy up for three days of pure North County charm—horses, pie, chili, and a tamale-fueled finale. It’s like stepping into a Norman Rockwell painting with better food and more horsepower. Bonus points for catching the crispy-fried glory of the classic car show while jamming to live country tunes.
SD Vintners Wine Festival
June 1, 2025
Is your love for wine borderline grape-obsessive? Perfect. Spend a dreamy day sipping unlimited pours from over 30 local wineries under the sun at the charming Bernardo Winery. Bonus: you get to pretend you’re a sommelier while holding a commemorative glass like you own the vineyard.
Music
PerreoLand Reggaeton Party
May 30, 2025
If your hips know better than your brain when a reggaeton beat drops, this is your Super Bowl. PerreoLand brings both the OG Daddy Yankee days and the new school Bad Bunny bangers under one frisky roof. One night only—shake it or regret it.
Party on the Pier – Freestyle Reunion
May 31, 2025
Pull out the Aqua Net and pump up the bass—this one-night-only throwback tidal wave is crashing into Broadway Pier. With legends like The Jets, Trinere, and Safire hitting the stage, it’s basically a mixtape come to life. Under the stars, with DJ Ace on deck, your nostalgia levels may reach dangerously fun highs.
Sports/Outdoors
Rock ‘n’ Roll San Diego Marathon & Half
May 31 – June 1, 2025
Ready to run through San Diego with 20,000 of your closest sweaty strangers while being serenaded by live bands? This citywide cardio party comes with a medal, music, and a chance to pass out in front of Petco Park with pride. Whether you’re in it for the full 26.2 or just the medals and post-race concert, it’s the city’s most musical excuse to wear compression socks.
Summer Movies in the Park: The Sandlot
May 31, 2025
You’re killin’ me, Smalls! Watch the greatest backyard baseball flick of all time under the stars at Standley Park. There are games before the movie and snacks for sale—so bring your blanket, not your glove.
