MAINopoly Returns to Santa Monica With Sips, Strolls & Street Games
The 11th Annual Board Game Festival Hits Main Street May 24
Main Street Santa Monica transforms into a life-size Monopoly board on Sunday, May 24, 2026. The 11th annual MAINopoly returns for Memorial Day weekend with a twist on the classic game that lets you eat and drink your way through the neighborhood.
The interactive tasting experience runs from 1 p.m. to 5 p.m. and turns Main Street’s restaurants, bars and eateries into playable properties. Participants exchange MAINopoly dollars for food and beverage tastings at over 20 participating locations, checking off spots as they go
This year brings a major upgrade. For the first time, guests 21 and older can sip while they stroll thanks to a special City of Santa Monica Entertainment Zone permit. Buy alcoholic beverages from the Go to Jail Beer Garden or select participating spots, then carry your drink as you walk from stop to stop.
The beer garden anchors the event with brews, beverages, music by DJ Richie Rich and lawn games. It’s a central hub where you can regroup, refuel and soak up the scene before moving on to your next tasting.
The food lineup spans Main Street favorites and Westside newcomers. La Vecchia Cucina serves Italian specialties. Library Alehouse pours craft beer. Lula Cocina Mexicana brings Mexican fare. Ubatuba Acai dishes out acai bowls.
Triple Beam Pizza features specialty pies. Rabano presents globally inspired plates. Jameson’s Pub pours drinks alongside pub classics. Tavern on Main serves up comfort food. Circle Bar mixes specialty cocktails. Papille Gustative plates French-inspired bites. Manchego offers Spanish tapas. JuneShine taps hard kombucha. Edgemar grills burgers. Ashland Hill prepares Mediterranean dishes. HomeState samples Texas-inspired cuisine.
MAINopoly 2026 is organized by the Main Street Business Improvement District. The event highlights local restaurants and bars while creating a Memorial Day weekend experience that feels more like a block party than a typical food festival.
Other activities include a Just Visiting photo booth, free rides up and down the street courtesy of Green Goddess Pedicabs, and an official after-party. The whole experience leans into board game nostalgia while celebrating Santa Monica’s dining scene.
Complete your game board by visiting every location, and you could win a Taste of Main Street Prize Pack valued at $1,000. The interactive tasting experience encourages guests to visit as many spots as possible, turning the afternoon into a friendly competition with delicious rewards.
The Entertainment Zone permit changes the dynamic. Instead of staying put at each location, you can move freely with your drink in hand. It adds a bar crawl vibe to the culinary tour and makes the whole afternoon feel more fluid.
MAINopoly welcomes all ages during the day. Families can enjoy the tasting tour together while adults take advantage of the new sip-and-stroll option. Monopoly-themed costumes are encouraged.
Tickets are available now at mainopolysm.com. Check-in happens at Ashland Hill, located at 2807 Main St. From there, guests can map their own route or follow the board game theme.
Main Street Santa Monica has long been a destination for dining, shopping and coastal culture. MAINopoly amplifies that energy by turning the entire street into an interactive tasting experience. You’re not just sampling food, you’re playing a game, collecting stamps and competing for prizes.
A portion of the proceeds benefits the Main Street Business Improvement District to fund community programming throughout the year. The festival showcases what makes this stretch of Santa Monica special.
Mark your calendar for Sunday, May 24, 2026. Dust off your top hat, grab your game board and get ready to taste your way through Main Street. This is one Monopoly game where everyone wins.