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About The Crafted Trail

We offer small group adventure travel tours that explore regional cuisines, farm based breweries, distilleries and wineries. We could not be more delighted that the farm to table artisanal food movement in America has become part of the modern collective conscious. To us, knowing the origins of our food has always been a way of life. We are excited to offer road trips and active travel tours that celebrate local food and support farmlands to sustain them for the next generation. Our team has over 20 years experience each working for the biggest names in the small group adventure travel market in the US, leading guests from all over the world throughout the USA, Canada and tours to Mexico.

upstate tours


Whether you’re looking for an upstate weekend getaway from New York City, a weeklong  National Parks hiking tour or just want to immerse yourself in


Click or hover over the photos below to browse all of our upcoming tours. We can also customize a trip to best suit your groups needs.

What We Offer

With over 20 years of experience, our staff has explored every corner of North America finding hidden gems off the tourist radar and our strong network of people keeps us current with new 'in the know' places.


Guiding people to beautiful places is our way of life. We have been doing it for over 20 years and love what we do, love

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While we travel with a set itinerary and deliver the destinations promised, we know every group is unique and no two trips the same. Sometimes

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Looking to escape New York City and visit the Hudson Valley region, but you’re a solo or single traveler? Are you without a car to

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We live on the road, we love what we do and we love showing you the things we are passionate about. Scenic hikes and adventures,

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Packing List

What to bring: Personal belongings and toiletries. A valid drivers license for citizens of the US and Canada. A passport for passengers from other countries

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Terms and Conditions

Before your trip: Payments: For trips under $300, full payment is due at the time of booking. Trips $301 and over require a non-refundable deposit

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Looks Fantastic!

I love what I am seeing! What else do I need to know?

Terms & Conditions

Our Team

Our experienced team has lead adventure travel groups for over 20 years

Jane Simos
Jane Simos
Lead Guide and Founder

Jane has been leading adventure travel tours for international clients throughout North America since 1997. She feels most at home on the road. An attempt

Jane Simos
jessica harris
Jessica Harris
Managing Director

The consummate multi-tasker and problem solver; Jessica brings us her knowledge and expertise of over 25 years managing adventure travel companies.        

Jessica Harris
upstate hiking tour
Jaime Alejandro
Office Manager and Tour Guide

Jaime’s unbridled enthusiasm makes the most mundane administrative tasks seem fun. On tour, his positivity is infectious and he shares it with all our guests.

Jaime Alejandro


We don't consider any question a stupid question. Ask away!

Contact Us

Got a question for us? Need guidance in selecting which trip will best fit your interests or schedule? Just want to drop in and say howdy or share feedback with us? Or our favorite, want to share some stellar photos you took on one of our trips? We love hearing from our past, present and future friends!

—Jane Simos, Owner


Mailing Address:
3328 US Highway 209
Stone Ridge, NY 12484


Proud to be the exclusive tour operator for Ellopia Films USA

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