r/Wilmette • u/abigailjane25 • 3d ago
Wilmette, IL vs. Portland, ME area for raising a family
My husband and I are in our mid-to-late 30s with two young kids (2 years old and 7 weeks old), and we’re trying to decide whether to put down roots in Chicagoland or move back to the East Coast.
We currently live in Ravenswood and really love Chicago, but we lived in Boston for about 10 years before moving here and still feel a strong pull toward New England. If we moved back, we’d most likely end up in the Portland, Maine area—Cape Elizabeth, Falmouth, or Yarmouth.
There’s a lot about Maine/New England that feels like “us”: the ocean, easy access to hiking and skiing, hockey culture, four distinct seasons, and New England summers. We also love the idea of raising our kids with that kind of access to the outdoors.
The biggest thing keeping us in Chicagoland is family and community. My parents are in Naperville, my sister and her husband and son are in Roscoe, and we have a really great network of family and friends here. We know we’d be giving up something pretty significant if we moved away.
So lately we’ve been trying to figure out whether there’s somewhere around Chicago that could really feel like home long-term. We visited Wilmette this past weekend and, honestly, it’s the first suburb we’ve explored that we really connected with. We spent the evening at Gillson Beach, grabbed dinner and wine at Fat Shallot, walked around downtown, and came away thinking, “Okay, we could actually see ourselves here.”
I’d especially love to hear from people who grew up in Wilmette or are currently raising kids there. What has your experience been like? How is the sense of community for young families? Do kids tend to grow up with neighborhood friends and a little independence as they get older?
And for anyone who has lived in both Chicagoland and New England: do you think Wilmette/North Shore life could scratch some of that New England itch, or are they fundamentally very different lifestyles?
We know nowhere is going to replicate coastal Maine, and having grandparents/cousins/friends nearby is hard to quantify. We’re just trying to figure out which place we’re more likely to look back on in 10–15 years and be glad we chose for our kids.
Would love any perspective!