Peter Gilmore Playground in Waltham has a dope-ass climbing structure. Its so cool that I’m surprised it’s legal in America. It’s a block off Moody St. If you’re not familiar with Moody St, it’s worth it for the restaurant scene.

Spy Pond Park in Arlington is good for really little dudes, but the playground itself isn’t worth a trip from the North Shore. Bonus: You can rent canoes and shit in the summer every now and then and paddle out to a little island. You’ll need to check a website or two to see when those are available.

You can rent a kayak from Paddle Boston. Launch from the Medford location, paddle upstream on the Mystic, there’s a little peninsula with a beach and facilities opposite the Medford Boat Club where you can disembark and picnic/swim. There is also a good playground there with things for toddlers to 5/6yos. Lots of green space for frisbees and soccer. There are also some pretty cool walking paths through the woods along the shore there. You eventually wind up on the dam that creates Mystic Lake.

Beaver Brook Reservation in Belmont has great hiking/picnic spots and a nice splash deck for the kids. It’s close to the Mighty Squirrel Brewery as well, so the adults can relax with food trucks and a beverage later. Mighty Squirrel is family/dog friendly with games and things for tweens and adults. Table tennis, cornhole, foosball…

EDIT: I can’t believe I forgot Connor’s Farm in Danvers. Jesus Christ. That place is the shizznit. Unbelievable playground. Bouncy thing. TRAIN RIDES! Holy shit. I love that place.