Community Running if you're open to track workouts! Pace inclusive, Monday and Wednesday nights. I know you said "casual," but if you're open to fast-casual, the energy is goofy and not intense.

Lamplighter Brewing ticks all of those boxes (and has great beer)

This is a good call.

I thought of 730 tavern too! I’ve definitely seen some family parties, like a gender reveal, there at the high top tables near the front windows.

There is a group called The Most Informal Running Club ever, they meet on Saturday mornings over by Herter Park at 10am. Many different rout options and lots of different level of runners. More casual than serious runners.

Smoke Shop next door also has a big bar, a variety of seating setups, is clean/bright/spacious, and has the advantage of smelling like barbecue.

It has its charms for sure but I’m not sure I’d call it “not grimy”. The decor is pretty vintage and there’s a sign on the bathroom door requesting you not to do drugs in it. If they needed to put up the sign…

The fresh pond loop or along the Charles river.

Somerville Road Runners has a lot of weekly runs. There's also Cambridge Running Club, but their setup doesn't sound like what you're looking for (they do a track workout on Thursdays and a long run on Saturdays). And a lot of local breweries have runs -- like I know Remnant Brewing in Union Square has a weekly run night.

Running stores tend to have casual runs, check both Marathon sports and Heartbreak Hill, there are also a couple of running clubs but not sure about their schedules

https://www.marathonsports.com/run-clubs/cambridge-run-group/

Ahh! I did not know that! Damn.

Notch Brewing in Brighton (but close to Cambridge) has runs on Thursday evenings and Saturday late morning. Good group, mix of paces, delicious beer.

Parkrun hosts a free 5k every Saturday morning at Dannehy Park, nearish to Porter. People are friendly and there's a wide range of speed.

Lord Hobo in Hampshire St used to be my go to with the stroller a couple of years ago, open early in the day and with a few high tops

During afternoons too? Every time I've been there for brunch I've felt like I'm at Applebees in terms of staff attitude

There is one in Davis Square that I don't know the name of. They meet by the T stop around 6PMish.

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I urge you to be extremely cautious jogging on sidewalks. Drivers, particularly when turning right, do not look for people (especially if they are coming against traffic) and rarely stop at stop signs.

The founder/owner of that place sadly has a history of sexually harassing employees IIRC.

The Lord Hobo in Woburn is a good spot for this then

Edit: maybe not a great place after all!

Every time I've been to foundry with kids, I've felt like a massive inconvenience to the staff. Not because we're being inconvenient - but the staff were of an attitude that kids should be there.

Pretty much any place can handle a 10 person reservation.

Cambridge Brewing Company is great - big space, pretty bright, not too loud or anything, and they have both good beer and some solid food. I've done some larger group stuff there in the past and it worked very well.

Russell House Tavern in Harvard, 730 Tavern on Mass Ave, and Foundry in Davis might be some other good options

Flatbread in Davis is nice for adults and kids. Not sure about high tops.

Notch brewery in Brighton (might be too out of the way) is great for gatherings - bus accessible and also easy to park at/near

Charles River Speedway is definitely worth considering.

You’re saying bar, but to clarify are you hoping to also do food? I’d make a reservation if possible, there’s realistically no other way to guarantee a high top area that seats 8-10 people.

Foundry on Elm has an area that would fit your needs. Bright inside and nice - easy parking, Easy access from the redline

From the same restaurant group could reach out to the independent in union square and see if you could use their bar/lounge space on the left side. I don’t think they typically open that side up until the evening, but not 100% sure. - that time of day should have reasonable parking and is easy access from green line

Olde Magoons saloon in Magoun square may not take reservations but you could contact ahead of time. Cozy Irish pub vibes with a slightly confusing menu, but good food and solid beer list. Easy parking and on the green line

Honorable mentions: five horses in Davis square, Russell house tavern in Harvard sq, Za in Kendall square (and they have an email request form you can use)