Fun Fall Trips

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"I’m so glad I live in a world where there are Octobers” -

Lucy Maud Montgomery, Anne of Green Gables

I love the Fall. Big Fall gal over here.

There are so many amazing things the Fall brings. Comfortable and crisp weather for refreshing runs outside. The leaves turning every kind of beautiful red orange color. An excuse to cozy up in a comfortable sweater. Picking fresh apples and pumpkins and snacking on cinnamon sugar covered cider donuts. Autumn brings lots of joy.

It’s a great time of year, and always seems to be one of the busiest times of year! That’s why I try to get a head start on some Fall activities in September, and plan opportunities to enjoy the season before it disappears!

There is still plenty of time left in October and November, so take advantage of it! Here are some suggestions on fun fall trips and things to do in the Tri-state area!

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Visit an Orchard for some Apple Picking

I’ve gone apple picking every year since I was born, and that’s without exaggeration. My family believes in tradition, and whether I could do it with them or did it with friends, my parents love that we still enjoy it close to 30 years later. We’ve been going to Barton Orchards upstate for most of those years, it’s been our favorite overall experience even in the cold and sometimes rain. Here are some other options in New York too:

This year I switched it up. First I went to Fix Bro’s Farm in the town of Hudson, New York. About an hour and a half upstate. It was lovely, and we got great apples because we went in peak Golden Delicious and Macintosh season.

Then we went to Solebury Orchard in New Hope PA.

It’s not a huge orchard but they had tons of apples, apple cider and donuts, and a nice shop where you can buy goodies! You can even pick fresh wildflowers or blooms from their garden for purchase.

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The best part is that I’ve never really gone apple picking with friends before, and this year I got to do it twice. And I even got Ryan to go to an orchard for the first time ever! In 8 years, I had never been successful in dragging him to pick some apples - football games always took up his Fall weekends!

Though I love going with my family so much, it was really fun to go with the gals, and then with again with a big group of friends! Funny enough, having a baby with us made me feel less like I was the kid enjoying it, and we were “going for the kids”. But if I’m being honest I still love it and will continue going back each year.


It’s Harvest Time - Head to a Vineyard

This is the time of year when grapes are harvested to make the wine. I have always wanted to learn this process myself, and hope I get a chance to do so this year.

I love wine, and I love vineyards. While many people think of a trip to a vineyard as a good spring and summer activity, it’s actually so nice to go in the Fall. Cooler temperatures for comfortably sitting outside, and really nice foliage.


Leaf Peeping Upstate - Take a Drive

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Maybe I’m biased, but the Northeast has the most incredible autumn. The leaves turn a bright range of colors from green to yellow to orange and red.

It’s October so many areas of upstate New York are past their peak but Westchester and Long Island (much closer to the city) are just changing now! And as you go into the Hudson Valley region it is totally peak! So it’s the best time to head upstate, even with no agenda, and take a drive. Check out the map below for the best areas this upcoming weekend and into the next week.

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Celebrate Oktoberfest + the Legendary NYC Marathon

Two of my favorite Fall days were cancelled this year. First was the cancellation of Oyster Fest down on Stone Street, which always feels like a big Fall kick off! Everyone crowds the cobblestone streets, drinking beers, enjoying live music, and eating bratwurst (if you’re me) and oysters (if you’re anyone else I guess/idk).

The second was the New York Marathon. I’m of course disappointed it was cancelled since I was a qualified participant - it was going to be my first marathon! But as a New Yorker, and someone who loved watching from the sidelines each year, it makes me so sad to know all the love and pride that day brings will be missing.

So why not celebrate these things anyway? Not in crowds, nor in objection. Just in happiness! Throw a little Oktoberfest party with your quarantine crew or even grab a drink at one of the traditional German beer halls like the following:

Lastly, Watermark Bar at the Seaport is doing their signature Oktoberfest. I’ve gone in previous years and it’s very fun!

For the marathon, there won’t be any race to watch on TV or runners to celebrate and cheer. But I’m going to be going for a run that day, and ending that run with a few beers. If you love that day like I do, celebrate it.


Decorating for Fall + Halloween

I don’t have a home big enough to store extravagant decorations for each holiday or season like my Mom does, but that’s my dream. I’m also not going to get trick or treaters in my apartment in Manhattan, but in Westchester I love decorating our house so kids will be excited to come get some candy! With that said, I barely celebrate it, but I do enjoy Halloween!

Over the years I haven’t dressed up much, but this year I’m pumped for it. Life is just weird this year so I’m ready to get weird. Don’t know what I’ll be yet, but I’ve got some ideas, and I’m hoping to have some fun with it.

Our friends Sammie and Christian had us over a few weeks ago and I’m SO inspired by her decorations. Check out her amazing porch!!


Fall Coastal Weekends

I’ve got some fun plans ahead to celebrate my friends’ 30th birthdays. I’ll be going back to one of my favorite trips this year, Newport! And looking forward to another weekend in Montauk! There are so many great fall activities to do in both places, and I’m excited to report back with more ideas here later on.


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If you don’t do anything else, grab some Halloween Oreos and stream some Hocus Pocus and Halloweentown. You’ll feel more festive for the season even just sitting on your couch.

That’s all for now! This Fall freak is signing off ;)

Xx Gab

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