Dust off your monocles and start practicing your best “Do not pass go!” because MAINopoly is back, and this time it's celebrating a whole decade of game board-inspired indulgence. On Sunday, May 25th, Santa Monica’s Main Street will once again transform into a culinary Monopoly board, where foodies, families, and folks in bowler hats will roam from Strand to Pier, collecting bites, sips, and Instagram fodder along the way.
Related: Things to do with Kids in Santa Monica
This isn’t your typical food crawl. MAINopoly: A Taste of Main Street blends a neighborhood block party with full-blown game night fever. Guests get a stack of "MAINopoly dollars" to trade in at 20+ participating restaurants and bars for curated tastings—from crispy soy honey cauliflower at Library Alehouse to squash blossom puff pastries at Papille Gustative. (Yes, you read that right—squash blossom puff pastry. It’s giving Mayfair-level luxury.)
Complete your MAINopoly game board by hitting all the spots and you’ll be entered to win the coveted “Taste of Main Street” prize pack, valued at $1,000. That’s a lot of cauliflower, even at Santa Monica prices.
But this is more than just a stroll and a snack. The event is peppered with Monopoly-themed mayhem: a “Go To Jail” VIP Beer Garden, DJ sets, lawn games, a “Just Visiting” photo booth, and even free rides up and down the street courtesy of Green Goddess Pedicabs. Think of it as Boardwalk meets beach town, with a much better soundtrack.
Feeling extra? Go VIP and you'll get early entry, two cocktails, exclusive VIP tastings, and access to that beer garden a whole hour before the general public even rolls their dice.
And if you’ve ever wanted to cosplay as the Monopoly Man, this is your moment. Attendees are encouraged to dress the part, and there will be costume contests—so yes, there will be top hats, canes, and hopefully zero real arrests.
Tickets start at $30 for GA, $55 for VIP, and just $20 for kids (under 5? They’re free to wander and sample juice boxes at will). Proceeds support the Main Street Business Improvement District, which helps keep Santa Monica’s Main Street weird, wonderful, and welcoming all year long.
Check-in starts at Ashland Hill (2807 Main St.) and the game runs from 1pm to 5pm. VIPs get a head start at noon—because even in Monopoly, it pays to have a little extra cash.
Grab your tickets at mainopolysm.com or Eventbrite, and bring your appetite, your competitive spirit, and maybe a friend to help carry all the tiny pizza slices.
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