Minuteman trail in Concord/Bedford/Lexington is lovely. Go there often and really enjoy it. There are historical plaques you can stop and read as well as bathrooms in the visitor center.

Also Lake Q in Wakefield (3.5 mile loop) is awesome and there’s a Farmer’s Market on Saturdays June - October.

Keeping with the cemetery theme, Forrest Hills in JP was my favorite outdoor place to stroll with infants. It’s beautiful. Arnold Arboretum is also a stroller friendly and beautiful place to stroll. I avoided Jamaica Pond because the paths weren’t as wide and sometimes with errant cyclists, determined joggers, and the occasional off leash “friendly” dog, I didn’t find the walk as enjoyable.

Check out the app/website AllTrails it'll give you a list of all the hiking trails in you're area and what the terrain is like and I believe it will even indicate stroller friendly.

The state parks system has a universal access program which includes a bunch of fairly level, wide, stable trails for people with limited mobility. I bet they’re also excellent for strollers. That link has a list of all the ones starting with those in the greater Boston area.

The Stony Brook Reservation has a nice 2.5 mile paved path in it.

The arboretum is obviously excellent.

Fresh pond, Cambridge. It’s about a 3 mile loop I think? Some parts are dirt/gravel but packed down and most is wide and paved. Also a nice bathroom if you need it. I also strolled around the Natick mall, it’s huge! The main grocery store there attached to the mall also has an awesome prepared food eating area that I enjoyed with my newborn. A bit more low key than the food court.

+1 for the mall suggestion, I’ve been to the Burlington Mall a couple of times and it was great for indoor walking. Our early 00’s mall dreams are alive!

Drumlin Farm in Lincoln- plus you get to see farm animals! You do have to pay to go, but it’s free with a Mass Audubon membership (which will pay for itself after a few visits and gets you in to all sorts of other fun nature preserves!)

Castle Island in South Boston is good... Everyone wins, kids see planes and boats and parents can take in the sights and be near the ocean as well.

Millenium park in dedham

Best piece of baby carrying equipment: baby carrying hiking back pack (osprey makes a great one). Once your baby can support their head with confidence, get one and open up the entire region. I opted for the hiking backpack 100% of the time over the stroller. Your hands are free. You view in front of you by your feet is open. And you don't take up as much space. It's much easier to get around the tight sidewalks around town.

Do you mean the rail trail/bike path? I agree it’s lovely but you’re often put at risk by maniacs speeding on bikes. Might not be relaxing environment for new mom with a newborn

Breakheart reservation in Saugus has a paved 1 mile-ish loop.

There are some great walks along the Charles river. It can get pretty busy in the BU/MIT areas but west of the city not so much. One point of caution- I've noticed ice can be a problem in the winter, and there often isn't sand or salt. I assume this is to keep it out of the river? Not sure. Either way I'd keep this a spring through fall activity

Check out the trustees of mass.

Most of the Esplanade, any of the reservoirs (Chestnut Hill, Brookline, etc), Arnold Arboretum

I know this sub hates it, but Seaport is great for strollers. Wide sidewalks, places to stop, snowport going on, etc.

It's too bad that the pond isn't better than it is for strollers, especially since it was just repaved, but you're absolutely right about all those things.

I agree but the Harborwalk is iffy with toddlers because there often isn't a proper fence blocking the harbor. OP won't have to worry about this for another year though.

At least Jamaica Pond doesn't have people driving vehicles on it. Can't say that for Forest Hills Cemetary. Why they allow anyone to drive around it is beyond me. Some idiot drove into the cemetery pond recently. Its a danger to everyone who walks around the cemetery. Take the T or park outside the main gate.

Mass & Cass at dusk

Rail trails are great for running with a stroller. The pavement tends to be very smooth- more so than your average sidewalk- and you’re often crossing fewer streets. Sometimes they are plowed, so it’s more passable after snowfalls than sidewalks.

The Somerville community path, the minuteman bikeway, the tri-community path in Woburn / stoneham, the trail in west Peabody, etc etc.

The arboretum would probably be my favorite place. Incredible beauty and paved paths and T accessible. Lack of bathrooms is the only negative

Castle island- Southie beaches

My 1 yo son loves it there!

Mt. Auburn Cemetery in Cambridge. Lots of trees and plants and shrubs and flowers and birds. Plus cool architecture and sculptures.

Honestly walk around Coolidge corner in the neighborhoods. It’s very stroller friendly and you will see lots of other people (often with bigger strollers!) doing the same.

And a 3 mile loop as well. Also paved

The Arboretum in JP is a great walk with a stroller.

No the actual Minuteman National Park. 😊 Agree about the bike path!

Leverett Pond in Brookline is very nice to walk around.

We also enjoy Forestdale Cemetery in Malden and Breakhart in Saugus/Wakefield

Horn pond

Greenway in Eastie! Can go all the way to Constitution Beach

Thanks for this idea! Checked it out today and it was great

Agreed. This was the best $250 I ever spent.

If you want a long-ish walk, Southie from Broadway T to the beach and back has a nice mix of commerce, residential and nature.

The Arnold Arboretum in JP has a ton of paved paths. I see people there with strollers all the time.

Neponset Trail in Dorchester. Wide, smooth paved paths and plenty of parking. It’s best in warmer months - wide grassy fields look a little bleak in the winter compared to other places.

The Neponset River Trail is gorgeous. It would be a straight shot on the Red Line but a long trip all the way out to Mattapan.

The part of the Boston Harborwalk that goes around UMass and the JFK Library. Beautiful views of the sea

Glad you enjoyed!!

Nut island has a lovely paved loop- and parking as well. Plus a nice wharf to walk down. And some beaches to walk along.

Love walking around Fresh Pond with the kids! DM me if you ever want company!