To go with bikes, scooters etc, we really love this helmet. It's light weight enough that my toddler will wear it. And it survived (unfortunately) one MAJOR digger and kept his noggin safe. Plus, it has the build in sun visor, which actually helps keep the sun out of his eyes, although not quite big enough to keep the sun off his face entirely. Starts at $26.
Turns out toddlers are slow, and pokey. So, if you need to cover great distances and they hate the stroller, a scooter is a great option. I love this one because it's very stable and turns easily. My son rides it 1.5 each way to and from daycare every day, so it really does hold up. $50.
Ergo 360 Mesh
If you plan to do any serious baby-wearing, this is one of the best carriers on the market. Do not be tempted by the Bjorn, even if it was in The Hangover. While most carriers pull from the shoulders, the ergo sits on your hips and makes baby-wearing actually tolerable. The 360 allows ergonomic facing both in and outward, so that when your kiddo is old enough ,they can see the world. I'd pay the extra 30 dollars to get the mesh version, because this can get toasty, especially in the summer. $175
For newborn carrying, I really liked the snugness of the moby or boba wrap. yes, it can get confusing to tie, but once you get it down, it's very easy. And it's great for the stage when they can't hold their head up. Roughly $35, but you can find these used on on discount sites as well.
It took me almost 2 years and 4 different strollers to figure out why everyone in Boston has this stroller. It really is the best. Every adjustment you need to make (And your toddler will demand a million) is done with the mindset that you'll be doing them WITH a screaming child WHILE someone gives you side-eye in line at the grocery store. Meaning: it all is fast and easy. And it has a small footprint, but is rugged enough for Boston's cobblestone. If you walk a lot, this is worth it.
Bumble Booster Seat
This booster seat is another great option for car seat families, or just to have if you're going to be out and about and may take a cab, because it's small enough to fit in your purse! FREEDOM. Your toddler needs to be 40 inches and 40 pounds, so grow kiddos grow. $26 dollars
Taxi-friendly Car Seat
For car free families, this car seat installs relatively easily (relative to basically any other car seat). And it's very light weight if you're taking it on trips. It's $58 on Amazon here (http://amzn.to/2hRKcws) but it typically runs around $49 at Walmart.com, so if you can get free shipping, you can buy it there.
Uppababy makes a great stroller, what can I say. And their umbrella stroller is fantastic. Lightweight and most importantly TALL. It's great for tall toddlers, and tall parents, so you don't feel like you're pushing around a doll's stroller. Sturdy enough that our never-stroller-napping toddler would occassionally zonk out in this. And you can fold it up to, well, an umbrella size. $259, so try to get it used, or resell yours.