Okay, so I’ve been meaning to explore the “5 Towns” area on Long Island for a while now. I kept hearing about it, but honestly, I wasn’t even 100% sure which towns were actually included. So, I decided to make a day of it and just go check it out.

First things first, I needed to figure out what the actual “5 Towns” were. Some quick googling told me we’re talking about:
- Lawrence
- Cedarhurst
- Woodmere
- Inwood
- Hewlett(which, it turns out, is further divided into Hewlett Bay Park, Hewlett Harbor, Hewlett Neck, and just plain Hewlett).
Getting My Bearings
I grabbed my phone, open a map app. Punched in the names, one by one, just to get a feel for where everything was. They’re all clustered together on the South Shore, pretty close to JFK airport, which I guess makes sense.
Hitting the Road
I hopped in the car and drove. My plan was simple, drive through the towns, one by one.
Started in, I guess, Inwood. It felt a bit more, well, working-class than I expected. Lots of small businesses, auto shops, that kind of thing. Then I rolled into Lawrence and Cedarhurst. The vibe shifted big time. More upscale shops, boutiques, nice-looking restaurants. I saw a few places that looked perfect for brunch, but I’d already eaten. Noted for next time.
Exploring a Bit
I parked in Cedarhurst and walked around a bit. Popped into a few stores, just browsing. Everyone was super friendly, I gotta say. It felt very…community-oriented, if that makes sense. Lots of families, people chatting on the sidewalks.

Woodmere was next. Honestly, it felt pretty similar to Cedarhurst, at least the main drag. More beautiful homes the further I drove in and the bigger the properties seemed.
The Hewlett’s
Then came the Hewlett section. Driving through, I could see why they’re broken down into smaller areas. Hewlett Bay Park and Hewlett Harbor, wow. Huge houses, waterfront properties, the works. Seriously impressive. Plain old Hewlett and Hewlett Neck felt a bit more…normal, I guess? Still really nice, just not as jaw-droppingly extravagant.
Final Thoughts
All in all, it was a cool little excursion. I can see the appeal of the area. It’s got a good mix of that small-town feel with some serious upscale living. I definitely want to go back and spend more time in each town, maybe try some of those restaurants I saw. If you’re looking for a little day trip from the city, or just want to see a different side of Long Island, I’d say it’s worth checking out.