40M Boston | Seeking Co-Conspirator(s) for Roadtrips and General Adventure
I’m hoping this is an/the appropriate place for this type of posting. Suggestions and guidance welcome as I’m (evidently) new at this.
The culmination of circumstance and coincidence have (not so) subtly indicated that the time is nigh for me to finally set off on all the adventures that have heretofore seemingly remained just out of reach on some distant horizon.
I’m 40, single, have lived what I consider to be an interesting life, have a successful and flexible career and I’m looking for one or more people who might be in a similar situation—seeking a reliable, honorable, genuine, funny, creative and interesting companion to share the trails, the road and the adventure with.
In the short-term (next ~9 months), I’m looking at some weekend / week long trips, given the present travel limitations and restrictions. Depending on how things shake up with work in the coming weeks, that could also include a month+ road trip. Towards the end of this year, I’m looking to embark on something semi-permanently, though I’m still defining what that will look like. One thing for certain, it will (at long last) include a winter spent elsewhere than New England.
I’m presently located in Boston.
It would be really cool if you were somewhere in New England.
Here are a few things to know about me:
- I’m ambitious, have a ton of energy (for adventure) and really enjoy the outdoors.
- I enjoy a wide range of interests/hobbies. We won’t run out of things to talk about anytime soon.
- People have a hard time describing me—I defy most paradigms, standards and norms.
- I’m a planner, insofar as I don’t want to find that I missed out on something incredible because I didn’t realize I’d be driving by it—or find out 8 miles into the backcountry that we didn’t bring the toilet paper. I’m not, however, someone who enjoys having every moment of every day planned out.
- I’ve put a lot of focus on being a good communicator and am fortunate to have met a few folks that have really enabled some good habits around that, specific to the circumstances of travel—being thrust into close quarters with a relative stranger in short time—and making it work, even when things get tough.
- I meditate, every morning, and I work to consciously be mindful. Grateful and present.
- I’m not looking for a relationship, but I’ve found my personality and interests are more aligned with women than men.
- I have a ton of gear, have spent a number of years involved in a number of outdoor pursuits am resourceful with finding good deals.
- I’m told I’m a great friend—reliable, dependable and thoughtful.
- I have an appreciation for old things--traditions, civilizations, literature, rituals and relics of bygone eras.
- I really like to see the sunset, whenever possible.
- I have been playing “name that tune” since I was old enough to remember music. You’ve been warned.
So what’s on my list?
- Pretty much anything outside, preferably temperate with more daylight than Boston.
- Lots of National Parks
- Many classic/epic hikes up to 2 weeks in duration.
- A pile of pages torn from Backpacker magazine with hikes and places I want to go.
- Alaska—the parts where you need a bush plane.
- Once the borders reopen, anything and everything overseas—I’ve only been to Iceland, Mexico and the Caribbean.
In the meantime, I’m big into winter hiking, am obsessed with trying “hot tenting” and I’d only need a reason to get on a plane to go anywhere South and West of Boston, at a moment’s notice.
TLDR: Have a flexible work arrangement (or similarly disinterested with “the grind” and need an escape) and want to travel with (arguably) the best companion you can find this side of the internet? Let’s chat.

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