Sponsored by Zappos.

Fall is my favorite season for countless reasons: the crispness of the air, deciduous trees shedding vibrant orange, red, yellow, and even green leaves with opportunities to curl up under a pile of blankets and light a match to throw on the fire. All of these plus steamy spiced cocktails and ciders, leather boots, and fuzzy hats encompass my pre-winter New England world late September through December.

When Blundstone asked me to share #HowIRoam, I instinctively imagined road tripping off to share someplace remote that I’d yet to explore — perhaps upstate New York, New Hampshire, or even rural Maine. But as time grew closer for my autumnal adventure I just couldn’t fathom leaving home, Nantucket, amidst the perfectly peaceful weather we were experiencing. After all, we only get so many coatless carefree fall days.

From the water to the woods, take a journey with me through some of my favorite fall scenes on Nantucket before winter sets in.

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Generally my favorite area of the island to spend an offseason day wandering aimlessly with a camera in hand, Madaket always feels majestic. Madaket also has two picturesque bridges, one within plain view of the ocean.

I’m what you’d call a ‘bouncy‘ adventurer. I like running around and climbing on things (attributed from my childhood years as a gymnast). I like to think I have pretty good balance most of the time.

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My Blundstones have amazing ankle support, supporting me in all of my active shenanigans.

I actually had a really fun and easy time ordering my boots, which isn’t always the case when I’m online shopping. Zappos had short video clips of each of pair making the ordering process fun and my decision making fast. And the fact that they have free shipping is always a plus.

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I grew attached to Madaket from spending so much time at a friends place overlooking the harbor a few years ago. We’d take long walks out to the tip of the west end of the island, Smith’s Point, great for a stellar sunset anytime of year.


Just a few blocks from the heart of downtown, I love walking Lily Street and turning down the grass path that leads to Lily Pond.

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October first is always an exciting time. It’s the start of Nantucket Bay Scallop season. Recreational scalloping kicks off. Soon after, you’ll find them on menu’s all around town. I prefer my bay scallops raw, straight out of the salty water.

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Alongside the path to Polpis Harbor, Holly Farm in the fall is filled with various landscapes, a few footbridges, bare and windblown trees, and drifting scents of the salty harbor.

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This little forested area feels like your New England Fall with a touch of unique. Squam is probably my most frequented place for adventuring off on my own. Far off of any busy road, you can really enjoy the sounds of nature and feel like you’re somewhere else all together.

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On a bench or in a tree, when I have the time, I bring a good book and post up, read and reflect. Squam Swamp presents you with the illusion you have the island all to yourself.

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When you want a view of the entire island you head up to the top of Altar Rock. With so many variations of paths to walk, run or ride each leading to a more beautiful landscape than the next, there’s someplace new to discover with each visit.

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BEACH #13b

Walk down the sandy path and up the hill to lookout upon cotton candy clouds and fiery sunsets or tuck yourself away from the wind in the little sand pit before you’re on open beach.

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Adventure is everywhere. There’s so much to explore in your own backyard. I hope you’ll add Nantucket to your list.

Thanks Blundstone and Zappos  for making this backyard adventure possible. As always, all words, thoughts, and opinions are my own.



  1. Nicki November 17, 2016 at 2:24 pm - Reply

    I have not been here yet and thought this would be a summer destination. You have totally sold me on a fall escape. Fall is my favorite season and I am always looking for new places to travel to during that time.

    Wonderful photos as well.

    • kristen November 18, 2016 at 1:09 am - Reply

      I hope you’ll come vita the island! It’s surely a special place anytime of year. Thanks for following along on our adventures 🙂

  2. Christie November 17, 2016 at 11:58 pm - Reply

    Gorgeous post!! Your photos are so beautiful and you capture the shoes in such an interesting way. I love Zappos! Such good deals and the shipping speed gets me every time.

    • kristen November 18, 2016 at 1:11 am - Reply

      Thanks so much Christie! I’m literally living in my Blundstones now haha – now if I could only get to Tasmania next 🙂

  3. Annette Richmond November 28, 2016 at 9:54 am - Reply

    I’ll definitely add Nantucket to my list, it looks beautiful! Thanks for sharing all your favorite hometown places, I know it can be a tough decision.

    • kristen November 30, 2016 at 9:19 pm - Reply

      It’s a wonderful little island! Anytime of year 🙂 Thanks for reading!

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