- February 23
South Shore Food Truck Festival
If the Boston Food Festival on October 5th wasn’t enough for you, head to Kingston (less than an hour from Boston) for the South Shore Food Festival on October 19th and 20th. The festival will feature over 40 food trucks, a Notch Brewing Biergarten, a 90+ Cellars Wine garden, live music, and more. This is a two-day festival that begins at 12 PM and ends at 5 PM both days, with VIP access starting at 11 AM.