1.9 min readBy Published On: May 2nd, 2025Categories: See & Do, See & Do0 Comments on Weekend Picks – May 2nd

Happy May Day and Derby weekend!

May Day is Saturday

Get ready, Charlestown — May Day is blooming this Saturday, May 3rd, and the neighborhood is throwing one big party to celebrate! From free workouts to floral installations, trunk sales to spritz tours, this day is packed with activities that’ll have you falling in love with spring—and your community—all over again. Read the full roundup here!

Derby Day is Saturday, too!

And they’re off!  It’s the 151st running of the Kentucky Derby at Churchill Downs.  20 horses will compete, and only one lucky winner will receive a $2 million purse!  The most exciting two minutes in sports begin at approximately 6:50pm on Saturday, May 3rd! Our top place to watch the race is the….

Ketel One Waterfront Derby Party at Pier 6

Join over 300 of your friends at the Pier 6 9th Annual Derby Day party! Prizes for Best Dressed, Spritz & Julep cocktails, photo ops & more!  Takes place on Saturday, May 3rd from 3pm-7pm.  Get your tickets here! 

Liquidation Sale at House of 44

House of 44 has chosen to close its doors to the boutique side of the business, but don’t worry – the salon will stay open!. This weekend, May 2nd, 3rd, and 4th, the boutique will mark down all of its items between 50 – 70% off (besides Charlestown merch, which will be 15% off). There will be also be a permanent jewelry pop up on Saturday!

Kids Day Out at the YMCA

Enjoy a quiet afternoon while the kiddos have a Kids Day Out at the YMCA on Sunday, May 4th 1 – 3 p.m. Registration is required with limited spots available. Free for members! Please email [email protected] to register today. Kids Day Out will include crafts, music and more!

Shop the new Mockingbird Baby & Kids!

Get excited — there’s a new kid in town (literally). Joy Street Kids, the local brand known for their playful, city-themed pajamas and super-soft kiddo staples, has officially taken over Mockingbird Baby Kids Clothing on Main Street!

SPORTS!

Kentucky Derby at 6:50 p.m. on Saturday

Red Sox vs. Twins – Friday, May 2nd at 7:10 p.m., Saturday, May 3rd at 4:10 p.m., Sunday, May 4th at 1:35 p.m.

Here are 9 places to watch the game in the neighborhood!

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