Customized and Multisport Tours

Customized Cycling Tours

Over the years, we’ve learned that every customer comes to us with a unique vision of their ideal Vermont cycling vacation. So, whichever self-guided cycling tour you choose, we can customize your tour in a variety of ways to make it your own special experience. Here are just a few examples but, by all means, bring us your ideas:

  • Begin your tour on the day that’s most convenient for you,

  • Stay for as many days as your schedule allows,

  • Cycle as many (or as few) days as you like,

  • Increase your daily mileage by combining stages or, adding options to your route,

  • Walk as an alternative to cycling (not available on all tours),

  • Choose the accommodations which best fit your preferences and budget,

  • Incorporate sightseeing excursions requiring a car into your itinerary by arranging the transfer of your vehicle by Diverse Directions from your tour’s starting point to one or more overnight destinations, OR

  • Make your cycling tour, a Multisport Tour!

Our Multisport Tour

For customers looking for a cycling vacation but want to experience a variety of activities as well, our Multisport Tour option may be just what you’re looking for. With its wide array of accommodation, dining and shopping options, Woodstock will serve as your base location while doing our multisport tour. Depending upon the number of days you’re able to stay, we will work with you to plan and arrange any combination of the following activities:

  • Cycle half-day loops from your base location, Woodstock,

  • Kayak the gentle waters of the Connecticut River (excursions offered by Great River Outfitters),

  • Hike nearby segments of the Appalachian Trail,

  • Swim, canoe, and picnic at Silver Lake in Barnard,

  • Zipline at Okemo Mountain in Ludlow,

  • Do some horse-back riding,

  • Visit Vermont’s only National Park, the Marsh-Billings Rockefeller Park (tour a Rockefeller family mansion) as well as the award-winning, historic Billings Farm and Museum,

  • Relax and enjoy Diverse Directions’ convenient shuttle service between Woodstock and the location of your daily activity.

Whether you’re looking to customize one of our cycling tours or doing our Multisport Tour, because Diverse Directions is locally based, our customers benefit from our intimate knowledge of the area. And, as our customer reviews attest, because we are a small, family-operated business, we have the capacity to respond quickly to the needs of our customers as those needs unfold during their trip.

To Order a Customized Cycling Tour or our Multisport Tour, This email address is being protected from spambots. You need JavaScript enabled to view it. to request a consultation with a Diverse Directions Support Representative.

Client Views

  • Booking with David saved our vacation! Perfect in every way. I can't recommend David and his services more. This isn't the kind of trip you want to go it alone! David thought of all the details to ensure we had the perfect bike routes and maximized our time. His selection of inns was spot-on -- a variety of properties all different but all special (and with FANTASTIC food and amenities). Can't say enough great things.

    - CatherineP on TripAdvisor
  • Wow! David is remarkable! Whatever seemed to go awry, whether a flat, another flat, rain or even support when I had to leave early, David had a back-up plan already developed when he sent a quick reply and made it happen! He was patient, kind and professional at all times. I recommend Diverse Directions Cycling Tours and would select them again in a heartbeat. So glad we found them.

    - Jill from the Biker Chicks on Google
  • Did a four day cycling trip in Southern Vermont, roughly 30 miles a day, through quaint small towns. We stayed at a charming local inn each night. David, the owner, provided us the routes to follow each day which were super. Roughly half on backroads and the other half on dirt roads which were quiet and picturesque. They collected our bags each morning to transport and were in communication each day with tips, weather and to check-in. We highly recommend to cyclists that love to get out on the bike but don't want to be bothered with logistics, planning the route and don't want to be a part of a group. Was perfect for us!

    - Michelle on Google
  • We had a terrific Trip! Thank you, David, for the excellent service. The cycling itinerary, accommodations, and dining recommendations were all fabulous. It was a lovely experience and we would highly recommend it!

    - Annemarie on Google

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7 Miles from Ludlow - A Documentary

Enjoy this video:

Tour Customization to Meet Your Needs

Dear Diverse Directions, I am beginning to research a bike trip for my mother, sister and I in Vermont for the Fall. We did our own trip in Europe per-Covid and rode 25 to 30 miles / day(mom on an ...

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Dear Diverse Directions, For the cycling tour we're planning to do in June, we will most likely fly into Boston (perhaps Hartford or Burlington) and would prefer not to rent a car.  We see tha...


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