Weekend Trip

Dutchess County, NY & Litchfield County, CT

Discover the Hidden Gems of the Northeast: A Luxurious 3-Day Gravel Adventure

Embark on an unforgettable journey through the picturesque countryside of Dutchess County, NY, and Litchfield County, CT. This exclusive, self-guided tour is designed for discerning adventurers who appreciate the finer things in life while craving unique experiences.

Traverse the charming back roads of Amenia, NY, and New Preston, CT, as you immerse yourself in the breathtaking beauty of this enchanting region. With each turn, you’ll be greeted by rolling hills, lush forests, and pristine landscapes that will take your breath away.

Rest and recharge at carefully selected, intimate inns that offer a perfect blend of comfort and character. These boutique accommodations provide a warm and inviting atmosphere, ensuring your evenings are as memorable as your days on the road.

Whether you prefer the challenge of a gravel bike or the ease of an e-bike, we have the perfect option for you. Our top-of-the-line e-bike rentals allow riders of all ages and skill levels to effortlessly navigate the scenic routes, making this adventure accessible to everyone.

Indulge in the freedom of a self-guided tour, where you set the pace and create your own unforgettable moments. Our meticulously crafted itinerary ensures you’ll experience the very best of Dutchess and Litchfield Counties, with plenty of opportunities for spontaneous detours and hidden treasures along the way.

Treat yourself to a luxurious escape that combines adventure, relaxation, and unparalleled beauty. This 3-day gravel getaway in the Northeast is the perfect way to recharge, explore, and create lasting memories.

Dutchess County, NY & Litchfield County, CT (Weekend Trip)

Dutchess County, NY & Litchfield County, CT (Weekend Trip)

Regular price $250.00 USD Deposit
Regular price Sale price $250.00 USD
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Day 1
Amenia Loop
Embark on your first day of adventure with a captivating out-and-back ride from the charming town of Amenia, New York. Nestled in the heart of the Hudson Valley, Amenia offers a perfect starting point for your gravel cycling experience. As you pedal along the scenic country roads, you'll be greeted by sweeping vistas of rolling hills, lush farmlands, and picturesque valleys. Take in the fresh air and bask in the natural beauty of this idyllic region.
Day 2
Dutchess County Loop
On your second day, set out on another exhilarating out-and-back ride from Amenia, this time exploring a different route that showcases the hidden gems of the area. Traverse the well-maintained gravel roads that wind through the countryside, passing by historic barns, quaint villages, and pristine nature preserves. As you immerse yourself in the serene beauty of the Hudson Valley, you'll discover the rich history and vibrant culture that make this region so special. Take a break at a local café or farm stand (of course all of our favorite stops will be included in the route!), where you can sample delicious homemade treats and mingle with friendly locals.
Day 3
Ride from Amenia to New Preston
This route takes you through the heart of the Litchfield Hills, a region renowned for its breathtaking natural beauty and charming New England towns. As you pedal along the winding gravel roads, you'll be treated to panoramic views of the Housatonic River Valley, with its gently rolling hills and pristine forests. Take a break in the enchanting village of New Preston, known for its unique shops, artisanal crafts, and farm-to-table cuisine. Finally, make your way to your hotel in the Litchfield area, where you can unwind and reflect on the incredible memories you've made over the past three days.


What’s included

  • Accommodations
  • GPS Routes + Travel Guide

What’s not included

  • Meals
  • Transportation or Transfers

Optional (with additional pricing)

  • E-Bike Rental(s) — $300 per bike

Single Occupancy


Double Occupancy

$900 per person

Register Today
Ready for an unforgettable weekend adventure?