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Our 2017 Dream Vacation Winner

Tyler Pyburn | 7/25/2017

There really is nothing like spending a week long vacation on the Cape in the summer. Especially if someone else foots the bill. The winner of our 2017 Dream Vacation Giveaway was lucky enough to kick off his summer with a complimentary week in a stunning Wellfleet home right on the bluff. Here's a little insight into how he and his friends spent the week!

What was your first response when you heard that you had won?

I couldn’t believe it - literally. I only vaguely remembered entering the contest (it was very easy to do!), and I figured this was some sort of unsavory marketing tactic.

Tell me about your personal history with Wellfleet?

Wellfleet is my spiritual home. From the age of seven through eighteen, I spent the majority of my summers and many off-season holidays on Northeast Pond at one of the modernist houses that was acquired by the National Park Service when they set up the National Seashore. My summers were filled with fishing, swimming at Gull Pond, camp at the Audubon Society, boogie boarding and surf casting (usually unsuccessfully) at Newcomb Hollow Beach, boating on the bay side with family friends, watching double headers at Wellfleet Cinema, trips to the Red Barn for mini-golf and candy, and forced marches around Great Island or on the Marconi swamp walk when my mother decided we hadn’t been active enough. When our lease on the house was over and I left Massachusetts for college, I continued coming down to Wellfleet in the summers staying with my father’s rental over the July 4th week and occasionally camping at Paine’s Campground or piling into tiny week-long rentals with friends. Then around 2009, the Cape Cod Modern House Trust began its work restoring the house I grew up visiting, and since 2010 first my father then I have been fortunate enough to be able to rent that house for the week of July 4th. Each year I invite friends from different parts of my life to join, and we have created a communal tradition. For 2017, I had begun looking into how we could rent a second house to accommodate our expanding group, and this is precisely when I learned that I had won the We Need A Vacation contest with choice of two weeks including the week of July 4th!

Who did you go down with?

Our group included my fiancee, friends since childhood, friends since college, and friends since graduate school. My father, step mother, sister, nephew, and Aunt were also down at house in Truro.

The 4th is always a great time on the Cape, did you spend it at the house or did you go somewhere in particular?

July 4th is truly a special day on the Cape, and every year we head down to Newcombe Hollow beach for a modest bonfire, BBQ, smores, and to catch the unofficial fireworks display that has emerged over the past few years. A big part of the plan hinges on getting a fire permit, which is limited to 10 for the beach (btw: kudos to the town of wellfleet for allowing these!). Last year I think I got the 9th or 10th, so this year I headed out at an unmentionable hour before sunrise to up my chances. Turns out I overshot by about 30 minutes but was happily rewarded with a fire permit for the effort.

What else was the week filled with?

We ordered a bunch of 2.5 to 3.5 pound lobsters from Hatch’s and feasted on those in many forms (lobster rolls, toasties, pasta) for much of the week. We barbecued, and my buddy slaved over the oven to cook delicious ribs. We hit up Mac’s and feasted on fresh and delicious sushi. To work off some of those calories, a bunch of us hit the Snail Trail in P-town, which is truly a hidden gem that I learned about only a few years ago from the kind host of Om-Sweet-Om. The more intrepid of our party hiked (actually ran) from Newcombe Hollow up to Provincetown with a plan to meet us at the beach at the end of the Snail Trail, but the timing didn’t quite work out. Of course, we fished, kayaked, and took in the fresh air and gorgeous weather from the decks and all over town.

What else made this week special? (Would love to hear how you just got engaged! Congrats again!)

Thanks! Yes, Chantelle and I got engaged in the Boston Public Garden a few days before we headed to Wellfleet. Having the house made it possible to share the post-engagement happiness with our dear friends. This was truly a special bonus.

Did the Jeep come in handy?

Very much so. We worked the logistics such that we were able to only rent one car (as neither Chantelle nor I have a car in Boston) for the trip to Wellfleet and then we had the flexibility of two cars on the Cape. The gorgeous weather let us keep the top down for all but one or two days. There’s something about that car that signaled vacation to my brain.

How was working with Kathy, the homeowner?

Kathy was a pleasure to interact with. The house was so well appointed, and she was very thoughtful about accommodating the two babies in our group. Not to mention how fantastic the property is with sweeping views of the harbor.

We are so happy to hear that Jon had a fantastic week in Wellfleet! Of course, it wouldn't have been possible without our sponsors: Cape Cod Jeep Rentals, Cape Cod Beach Chair, and The Furies.