Fall Traditions: Apple Picking at Hilltop Orchard


There’s nothing like Autumn in New York – crisp temps, fall fashion, foliage, orchards, vineyards, pumpkin patches, apple cider donuts …

and the list goes on and on.

As kids, at the beginning of every Fall season, Dad would fill up the family car with as many cousins as possible for a day of apple picking just a little north of the city. I never knew exactly where our destination was, and I’m still not quite sure where we used to go. But I can vividly remember being glued to the windows, admiring the fall foliage against mountain roads and the exhilaration of cradling my very own bag of freshly picked apples on the long ride home. A day of apple picking always felt a bit like a fairytale for me. So, it’s no surprise that I couldn’t wait to continue the tradition with our little one this year.

Before you head to the orchards, apple picking in the Northeast typically begins in early September, with some farms offering varieties ready by late August, and ends in October. However, the more popular orchards may be picked through before the end of season, especially those closest to New York City. With so many farms to choose from, a few weeks ago, during our trip to the Berkshires, we headed to Hilltop Orchards & Furnace Brook Winery, located on the border of Massachusetts and New York, for a perfect day of apple picking, wine sipping and family time. With Covid and social distancing measures in effect, Hilltop is not currently offering its usual wine tastings, but you can still buy a bottle of their wine, cork and enjoy while apple picking (and enjoy we did)!

For our very first family apple picking trip, we had to have the perfect mommy and me looks. With all this time spent indoors, we haven’t had the opportunity to take very many family portraits, so I couldn’t let this opportunity to snap some shots go to waste! As a new boy mom, I’ve come to learn that getting matchy, matchy with your baby boy is not exactly an easy task. Apparently, no one makes mommy and me outfits for mamas and their little boys (hmph). But, I’ve taken the challenge in stride and am glad that I’ve been forced to use a bit of my own creativity to create coordinated looks with our little guy.

For baby, I opted for something a bit farm inspired and went with a yellow oxford onesie, denim shorts, suspenders, and denim slip-on shoes. I wanted to be coordinated with our little guy, but a touch whimsical and wore the most beautiful yellow cotton and linen maxi dress from Mara Hoffman, a pair of flat brown leather sandals, thick gold twisted hoops and my hair tied in a loose pony with a white floral bow (also comes with a matching mask). I couldn’t have dreamed of a more special day and baby seemed quite pleased too!


Oxford Onesie | Ralph Lauren, similar style here || Denim Shorts & Suspenders | H&M Denim Shorts & Suspenders || Baby Shoes || Gap, similar style here || Dress | Mara Hoffman Philomena Belted Dress || Hair bow | Free People Mask & Bow Set || Earrings | Lili Claspe Gina Hoops

Photography | Reluctant Husband

Location | Hilltop Orchards & Furnace Brook Winery

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