
A boutique tasting walk through Little Italy's shops and galleries in costume, ending with a costume contest and DJ.
The Little Italy Halloween Wine Walk returns to Little Italy on Saturday, October 24, the weekend before Halloween. It's a boutique tasting walk that takes you through the neighborhood's shops and galleries, with the route covering India Street and the Little Italy Piazza. The whole thing runs from 4 PM to 7 PM, so it's a late-afternoon thing that lets you spend a few hours drifting from one spot to the next.
The format is straightforward: you wear a costume and wander through the participating shops and galleries, stopping for a pour at each. It's a tasting walk, so the point is to sample rather than settle in at one place, and the route keeps you moving between the storefronts and the piazza. Once you've worked your way through the tastings, the walk ends with a costume contest and a DJ, which is where the costume part actually pays off.
It's a good way to see the neighborhood on foot, especially if you're into the gallery side of Little Italy. You'll be popping in and out of different spaces along India Street, so it's as much about the walk as it is about the wine. The costume contest and the DJ at the end give it a party feel that carries over from the tasting part of the afternoon.
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Entry is a $40 wristband, which gets you 12 tastings. The walk runs from 4 PM to 7 PM on Saturday, October 24, across the shops, galleries, and the piazza in Little Italy, San Diego.
Date
Saturday, 24 October 2026
16:00
Price
Paid
Recommended Age
+18 years
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