What to Do This Weekend on the South Shore August 29-30
Looking for something fun to do this weekend? From waterfront festivals to live music and oceanfront markets, there's no shortage of reasons to get out and enjoy the South Shore.
Plymouth Waterfront Festival - August 29
Spend Saturday along Plymouth's historic waterfront at this free, family-friendly festival hosted by the Plymouth Area Chamber of Commerce. Beginning at 10:00 AM, the event features a classic car show, a duck race, local vendors, live entertainment, and plenty of family fun.
Learn more: https://irishboston.org/event/plymouth-waterfront-festival/
The Smoking Jackets at The CabbyShack - August 29
Keep the fun going Saturday night with live music from The Smoking Jackets, one of New England's premier party bands. The show starts at 9:30 PM at The CabbyShack on Plymouth's waterfront.
Learn more: https://www.cabbyshack.com/event/the-smoking-jackets/2026-08-29/
Shop N' Sip at ThreeV Sand Bar - August 30
On Sunday beginning at 12:00 PM, browse local vendors while enjoying ocean views at the final Shop N' Sip event of the season. It's the perfect opportunity to shop local, grab a drink, and spend the afternoon by the water.
Learn more: https://seeplymouth.com/event/live-music-sundays-at-the-sand-bar-at-cordage-park-plymouth/2026-08-30/
Bad Decisions 80s Beach Bash - August 30
Wrap up the weekend with an afternoon of throwback hits at ThreeV Sand Bar. Starting at 2:00 PM on Sunday, this free, family-friendly beach party features live music from Bad Decisions, food trucks, and beautiful waterfront views.
Learn more: https://thepickpocketsband.com/event/6676333/773619911/bad-decisions-threev-sand-bar
Whether you're looking for family fun, great live music, or simply an excuse to spend time by the water, this weekend is packed with great events across Plymouth and the South Shore. Enjoy!
