Okay, folks, let’s talk about escaping the concrete jungle for a bit! I’ve been feeling super cooped up lately, so I decided to plan some day trips from Long Island, NY. Here’s how I went about it and what I discovered.
First, I brainstormed. I mean, really brainstormed. I grabbed a pen and paper, no fancy apps, just old-school list-making. I jotted down everything that sounded remotely interesting within, say, a 2-3 hour radius of Long Island. Beaches, hiking trails, cute little towns, historical spots… you name it, it went on the list.

Then came the research phase. I hit up Google, plain and simple. I typed in things like “best beaches near Long Island” or “historic towns near NYC”. I skimmed through a bunch of articles, travel blogs, and even some TripAdvisor forums. I wasn’t looking for anything super detailed at this point, just trying to get a general feel for different places and see what sparked my interest.
Narrowing it Down
My initial list was HUGE. Way too ambitious for a bunch of day trips. So, I had to prioritize. I thought about what I was really in the mood for. Did I want a relaxing beach day? An active hiking adventure? Some charming, small-town vibes? This helped me chop the list down considerably.
I also considered practical stuff, like travel time. I used Google Maps to get estimates for driving distances and checked for public transportation options, just in case. I didn’t want to spend half the day just getting there and back!
My Shortlist of Ideas
- Fire Island: I figured the ferry ride would be a fun part of the adventure, and the beaches are supposed to be amazing.
- Cold Spring: I’d heard about its cute shops and antique stores. Plus, it’s right on the Hudson River, which is always a plus.
- Beacon: Another Hudson River town, and home of Dia Beacon which I thought could be fun.
- North Fork: For all the wineries and Farm Stands.
Making the Final Decision(For this First Trip!)
After looking at some pictures online and checking the weather forecast (super important!), I decided to make Cold Spring for the first day trip. I was really craving a mix of nature and browsing, and it seemed like the perfect fit. The plan is to take the train.
So that’s where I’m at! I’ll let you guys know all about my actual trip to Cold Spring after I go. Stay tuned for more day trip adventures. Wish me luck it isn’t too hot!