Last updated on November 20, 2023 by Liza Hawkins
Enjoy a long wintry weekend in the Adirondacks surrounded by breathtaking mountain views, winding rivers and glassy lakes, apple orchards galore, with a myriad of charming Upstate New York towns peppered in-between.
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Living on the East Coast had its perks. I often said we were lucky in Maryland to be so close to a number of great weekend road trip destinations: an hour from both Baltimore and Washington D.C., four hours from New York City, two-and-a-half hours from Philadelphia, three hours from Charlottesville — the list goes on and on.
Now that our kids are older, and since we’re no longer on the East Coast, my sister and I have pledged make time to get away and explore cute towns all around the country together a few times a year.
A Wintry Weekend in the Adirondacks
We had our first getaway in November 2018 — a wintry weekend in the Adirondacks! — and used a few key parameters (location, lodging and activities) to help define our inexpensive weekend road trip.
Once we settled on a general area in upstate New York, we scoped out Airbnb to find the perfect space.
There are a lot of options for two people in autumn and winter that fall within the $100-140 price range per night, or even four people if you double up in rooms.
Our hearts were set on a cabin or something that evoked a warm, woody feel, and we wanted a house to ourselves. We weren’t looking for wilderness-level rustic or camping — running water and indoor plumbing were a must — but were fine with being out in the woods in a place that felt a little quirky.
Turns out we found a new cabin with exactly what we were looking for, and it couldn’t have been any more charming!
Gerry and Susan are Airbnb “Superhosts,” which means they’re experienced and highly rated by their guests.
We loved the small touches that made it feel homey, as well as the smart ways they made good use of the small space, including a card table hidden away that worked perfectly for our puzzles.
The view from the screen porch looked directly upon the small town of Wells, which (especially after a snow) looks like like a postcard.
It didn’t take us long to feel right at home! Here’s how our weekend went…
Friday: I drove five hours up to Brooklyn.
I ended up taking the day off work so that I could drive up to my sister’s apartment after my kids were off to school, which meant we could get away early Saturday morning, as opposed to making Saturday an entire day devoted to travel.
I arrived just after dark, we ordered phở take-out and then went to bed early.
It doesn’t sound like much to be excited about, but it’s hard to find phở as good as what’s in Brooklyn, so I always savor it when I’m there!
Saturday: We left first thing for the Adirondacks.
My sister’s son wakes up early like most kids, so we were up and ready to go between seven and eight in the morning.
We’d mapped our route ahead of time and planned to stop for three things on our way to the cabin: groceries, hard cider and lunch in Woodstock. And, with our only goal to get there before dark, we also agreed that we’d stop on a whim if something looked interesting — why not? It’s just the two of us!
Just outside the city we stopped into Trader Joe’s for our weekend groceries. We figured it’d be cheaper to buy them there rather than in a smaller town, and it meant once we got to Wells we wouldn’t have to leave the house for the rest of the evening. Yesssss…
Once done, we paused in the parking lot to search for cideries along our route to Wells, then hit the road again and drove another hour or so until we reached New Paltz in the Hudson Valley.
Note: glorious fall colors were still on display just outside New York City! That would change as we neared our destination…
There are a few different cideries and orchards in New Paltz, but be careful in fall or winter because some were already closed for the season when we drove by in mid-November.
We landed at the Dressel Farms market stand which had tons of apple varieties, apple products (like pies and cakes), as well as regular cider.
We grabbed a jug of cider, figuring it’d be yummy by the mugful over the weekend while we worked on our puzzles or watched a movie. Warming it up on the stove would have the bonus effect of making the house smell good, too.
Then we walked about a hundred feet down a hill to a warehouse space occupied by Kettleborough Cider House, where they’ve been brewing their own small batch hard cider since 2012.
For five dollars each, we did a tasting of five different hard cider varieties before grabbing two bottles to take with us for the weekend. And we got to keep the stemless tasting glasses!
The only downside to that visit were the copious amounts of fruit flies, which the brew master said is par for course with a sweet beverage being made in such a small, warm space.
Once we finished our tasting, we made our way another forty-five minutes north to Woodstock, where we planned to have lunch and walk around a little in town. It was about noon once we got there and downtown Woodstock was bustling, despite the cold and blustery weather!
It took a while to find parking and each of the restaurants we’d mapped out had at least a twenty minute wait to be seated — even for a party of just two people.
We finally got a table at Oriole 9, a big open restaurant space serving breakfast and lunch farm-to-table style. My sister’s a vegetarian, so we also need to ensure the places we eat have a decent variety of non-meat options to pick from so she’s not relegated to “garden salad.”
Oriole 9 didn’t disappoint! We each got a rueben, mine made the traditional way and hers with tempeh instead of meat. They were both delicious!
If you ever eat at Oriole 9, make sure to check out their floor-to-ceiling “specials” blackboard before ordering off the menu. Lots of yummy treats there!
Finally we hit the road one last time to try and get to Wells in the Adirondacks before dark.
We came close, but ended up arriving just after sunset and to snowy conditions! We were grateful to already have groceries.
Turns out the storm that blew through also knocked the power out. The hosts called us just after we’d arrived to make sure we knew, and to let us know a generator would keep the lights, heat, fridge and other necessities going until it was restored — no stove or oven, though.
That news sealed the deal on what to make for dinner: cheese plate!
We opened up the card table and got to work on one of our puzzles and devoured the cheese, crackers, fruit and nuts.
Then, off to bed early, because … why not?
Sunday: We planned our most active day.
We were staying in a beautiful part of Upstate New York and it seemed a shame to visit and not take in at least some of what the Adirondack Mountains had to offer.
My sister and her husband have enjoyed hiking and backpacking for years — they planned the Dolly Sods trip we did in 2013 for her thirtieth birthday and often take little day trips now with their toddler son.
They found a trail about forty-five minutes from our cabin that looked to be a simple hike ending with breathtaking views from a fire tower at the summit of Hadley Mountain.
We planned to head out after a slow morning (more puzzles!) with a hearty late breakfast, and a goal of returning to our cabin before dark to settle in for the night.
I wasn’t looking for another Dolly Sods repeat, and neither was my sister, despite how much fun it was that time. We wanted to hike for a few hours, enjoy the beautiful mountain landscape from up high, and then get back to our cozy cabin.
Being that it was just the two of us, and aside from a goal of being home before dark, we allowed ourselves the option of stopping along the way if we saw a spot that looked picturesque.
It was nice being carefree about logistics and we were able to enjoy all kinds of beautiful scenery we’d have missed otherwise, like stopping at the Great Sacandaga Lake to catch the last gasp of fall color on the surrounding foothills and take in the woodsy lakeside landscape.
After about a half-hour we climbed back into my car and made our way to the trailhead, which was at the bottom of a tense drive on an unpaved (and pretty snowy) steep road ending in a little parking lot.
We were a little nervous about my Jetta making it back up that road when we were done, but I’ll spoil the suspense now and reveal that we made it up and out with no issues at all. Word to the wise, though, if you visit when the weather’s bad: Road conditions to the trail could be dicey.
That said, the rest of the roads were absolutely fine. Kudos to the plowing work in New York!
It’s true that the Hadley Mountain Trail hike itself wasn’t difficult … in the best of conditions.
We weren’t there in the best of conditions, though.
It was definitely trickier than we anticipated due to the snow that’d fallen a day earlier and the resulting icy, snowy, slushy steep trail.
We did a lot of slipping and sliding and had to take breaks along the way to catch our breath, but in the end the two hours spent getting sloooowly to the summit were well worth the laborious trek.
And, thankfully it only took a fraction of the time to get back down to the car and neither one of us was injured along the way. Ha!
We ended the night with a recipe for Cacio e Pepe my sister found (the technique reminds me of how I make Spaghetti Carbonara), bagged salad from Trader Joe’s, toasted buttery baguette and a glass of sauvignon blanc.
Plus — you guessed it — more puzzle.
Monday: We planned our least active day.
And thank goodness we did.
Both of us were exhausted — and I was also quite sore! — from the previous day’s hike. We woke up, worked on the puzzle, ate breakfast, worked on the puzzle some more and then decided to drive around for a bit, sight see, and then grab lunch before heading back to the cabin.
We made our way to nearby Speculator, known as the “All-Season Vacationland,” to take some photos and grab lunch at Sunrise Diner.
The diner was clearly a local haunt.
My sister and I appeared to be the only vacationers in this “All-Season Vacationland” called Speculator, and while we may have felt a little out of place at the diner, that didn’t stop us from ordered a feast of fried foods for lunch, along with our choice of soda can … from a nearby mini-fridge.
Aside from the lingering griddle-and-deep-fryer-grease smell that clung to our clothes, we had a very nice time.
Afterwards we hit the road and took the long way home with a plan to stop and take photos along the way, and another goal of getting back to the cabin before dark.
And then, back we went to the cabin for face masks, hot cider and the start of our second puzzle — a two-thousand piece monstrosity that despite knowing we wouldn’t finish before leaving, we gave our best effort anyway.
It took TWO card tables to fit that puzzle (and oddly enough, our hosts had two at the cabin)!
Tuesday: We headed back and I kept going to Maryland.
It snowed more overnight and into Tuesday morning, which meant we lingered around the cabin until close to ten in the morning to ensure the roads were in decent condition before setting off for Brooklyn.
After breakfast we packed up, took some more photos of the cabin and the property, and then hit the road, stopping to grab a few last photos of the town of Wells where we stayed, as well as nearby Hope.
I’d considered staying overnight at my sister’s apartment again, rather than driving all the way home to Maryland, but in the end thought it’d be nice to just be home. So, home I went.
Our next weekend road trip takes us back north, but this time we’re staying in the Hudson Valley, a little closer to Brooklyn than the Adirondacks, and equally as charming.
Get more tips for how to plan an inexpensive weekend road trip here!