The Adventures of Scott and Caroline: Upstate New York Roadtrip: Part 1

May 23 - 24, 2015
Islip and surrounding areas, Long Island, NY

We're not in Manhattan anymore!

As planned, we recently ventured out on a driving tour into Upstate New York for nine days over Memorial Day week. It was our first trip of any length since moving to NYC over three months ago and we were excited to see what our new home state had to offer. The areas just north of the city (referred to as Upstate New York by anyone who lives in New York City), specifically the Hudson Valley which runs along both sides of the Hudson River, connected by several bridge crossings, and the Catskills Park region just to the northwest of the Hudson Valley proved to be positively beautiful, with lots of leafy trees, green grass, misty mountains, rivers and waterfalls and we packed a lot of sights in on our driving adventure.

To kick off our trip, we spent just one night, Saturday, at a Hilton Garden Inn on Long Island just to the west of anything that might be considered fashionable, due to price and central location concerns. After a travel-heavy morning and leaving the bulk of the Long Island traffic behind, we relaxed a bit over lunch at a cute, old-school diner.

First stop, Cutchogue, NY!

After lunch, we drove out to the end of the North Fork where you can catch a car ferry to Connecticut (so tempting...).

At Orient Point, NY, looking across Long Island Sound, with the car ferry to Connecticut in the background

The trip to the tip of the North Fork to check out Long Island Sound and stare across the water to Connecticut was bookended by some lovely wine tasting, also in the North Fork, first at Bedell Cellars.

We shared a tasting at Bedell, which was a good thing because the tasting pours were HUGE!

And then at Croteaux, a rosé-only winery. We enjoyed the wines at both and would definitely return!

Enjoying the sunshine and rosé at the oh-so-charming outdoor tasting room at Croteaux

Charming, old-but-pristine, white-washed churches with tall, narrow steeples appeared on every block, in between the farm stands (not as plentiful as I had imagined, but it was early in the season) and plant nurseries. "Why are people on Long Island buying this many plants?" I was forced to wonder. I had read about how idyllic it was up here, but quite frankly, while perfectly pleasant, aside from the wineries we visited, it fell a little short of my expectations.

On Sunday, we checked out of the hotel and headed west and north to the Hudson Valley. But before continuing on to the charming small towns of the Hudson Valley, we planned a couple of Long Island stops on our route. First, we visited Sagamore Hill National Historic Site, the summer home of Teddy Roosevelt and his family. The home itself was actually closed for renovations but the park ranger on duty invited us to wander the grounds, free of charge. This was fine with us, as we rarely take the time to tour historic homes anymore. The old adage "you've seen one, you've seen 'em all" truly does seem to apply here and when you've traveled as much as we have, well...

Scott does his best Teddy Roosevelt pose on the porch at Sagamore Hill

After we skulked around the closed-up house for a bit, peeking in the windows and such, we took the short nature trail to the small beach and wetlands area, which was quite lovely on a warm spring morning.

The beach at Sagamore Hill

Our next stop was Sands Point Preserve, which proved to be truly worth skipping unless you want to pay $10 to picnic and swim at a small, uninspiring beach.

The grand homes just beyond the meh public beach - no riffraff allowed

The most noteworthy sight here is the enormous turreted former stable and servants quarters from back in the roaring '20s Gold Coast days of the Vanderbilts, Chryslers and Guggenheims, which is now a visitor center, adjacent to the giant parking lot. It is shocking to think that horses once lived in such a grand structure!

And fro here, it was on to Hudson Valley for the next phase of our road trip! Stay tuned!

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