About This Tour
Where We Go
Tour Highlights
Tour Cost
Brief Tour Description
Key Dates
Minimum Number of Tour Members
How To Book This Tour


This tours travels to some of my most favorite places in New England. These are the towns and villages that we go to for that special vacation, quick weekend get-away or that I show to my out-of-state friends when they come to visit. We stay in three quintessential New England towns that are frequently ranked as the prettiest in each state. Each town is surrounded by great riding and a multitude of things to do off bike.  This tour highlights the crème de la crème of northern New England riding and hospitality.

DATES 2024: July 11 – 18
DATES 2025: July 10 – 17
DURATION: 7 Riding Days/8 Nights
START/FINISH: Chesterfield NH/Hampton NH
DISTANCE: 200 – 280 miles per day – Asphalt roads
DIFFICULTY: 3 out of 5
STATES VISITED: Vermont, New Hampshire, Maine
LAYOVER DAYS: 1- Stowe, 1 – Jackson, 1 – Wolfeboro = 3 Total (can ride or rest)
ACCOMODATIONS: 3 to 4 star hotels and inns – classic historic early New England style



  • Day 1 – Chesterfield (NH)
  • Day 2 – Stowe (VT)
  • Day 3 – Stowe (VT)
  • Day 4 – Jackson (NH)
  • Day 5 – Jackson (NH)
  • Day 6 – Wolfeboro (NH))
  • Day 7 – Wolfeboro (NH)
  • Day 8 – Hampton (NH)


  • Special Places – Stowe, Jackson and Wolfeboro are all quintessential classic New England destinations
  • Special Roads – Mt. Equinox Skyline Drive, Whiteface Veteran’s Memorial Highway, the granddaddy of NE mountain roads – The Mt. Washington Auto Road plus several other memorable rides
  • Special Stops – Lunch Lake Champlain, Mount Washington Hotel, Marginal Way – Ogunquit
  • Special Things to Do  – Rock of Ages Granite Quarry, Cog Railway Mt Washington, Longest Single Zip Line Cable on East Coast, Boat Rides on Lake Winnipesaukee

MOTO-CHARLIE reserves the right to alter the exact route at his discretion.


The cost for this tour at the current exchange rates will be:

  • Single rider in a single room
  • Couple riding two-up sharing a double room

These cost numbers should cover your direct tour costs including all hotels, all meals, gas and my fee. Please note that these tour costs also reflect high season hotel rates in effect from July 1 through September foliage season.


This tour focuses on the three New England states, touching on all the beauty that showcases their classic New England essence. We get to vist several famous mountains, lakes, villages and end up with a short taste of New England’s famous coast line. There is plenty of off-bike activities too, from hiking, to zip lining, to boat rides on the lakes to simply relaxing on the porch while practicing your people watching skills. 

Most people like to arrive at least one day ahead of time to rest, see the local sights, ride the area around our base or maybe just to meet the other riders on the tour. If that is you then I  offer a free 1/2 day ORIENTATION DAY to all Tour Members. I’ll be more than glad to help you plan whatever activity might be of interest to you.

  • Day 1 Today we start from our base in southern Vermont and work our way north. We will ride through some of Vermont’s most classic postcard perfect little villages. The famous Route 100 in central VT will be our guide. This road frequently shows up on the top 10 roads to ride in the US. In Europe the roads that go over the mountains are called “passes”, in Vermont they are called “gaps”. We will detour a few times to ride several gaps back and forth over the spine of the Green Mountains and then rejoin Rte 100 to end the day at our very Vermont style hotel in Stowe.
  • Day 2 We will spend the day flirting with Lake Champlain, both riding along it and across it. This is the 6th largest lake in the US and is partly in Canada. At 125 miles long you can connect to Manhattan to the south via the Hudson Rivers or go north all the way out the Atlantic Ocean via Montreal and the St. Lawrence seaway. Today we will sneak out of New England for a short bit, via ferry across the lake, so that we can ride up the Whiteface Veteran’s Memorial Highway. At 4,867 feet it’s the 5th highest mountain in New York and the only one with a paved road to the top. The 360 degree views from the top, including Lake Champlain and the Vermont mountains are spectacular. We then work our way back along the lake, cross back into Vermont on another ferry and ride an idyllic loop back to Stowe.
  • Day 3  – Today we ride some of the less visited roads of Northern Vermont getting up close to the Canadian border. There is some great riding up north as we pass by Jay Peak and its excellent ski resort, which gets the most snow of any resort in eastern North America, averaging almost 32 feet a year. From there we work our way east to the Burke Mountain auto road for a nice lunch. After that we cross the border into New Hampshire as we wander part of the White Mountains before reaching our historic lodging in Jackson.
  • Day 4  – Hopefully the weather cooperates because today we ride the best and highest of what the White Mountains have to offer. The highlight of the day will be the Mt Washington Auto Road, which goes all the way to the top at 6,288 feet. The road is approx 8 miles long, narrow in some places and roughly 1 mile is hard packed gravel. The highest measured windspeed in the world of 231 mph (not due to tornado or cyclone) was recorded at the top back in 1934. It still is closed to motorcycles on occasion if the wind is high or the weather is bad. Otherwise it is a spectacular, unforgettable ride. In Vermont the roads over the mountains were called gaps. In NH they are called “notches”. We will ride a few of the more famous notches as well as one of the better known mountain roads, the Kancamagus Highway, noted for its fabulous Fall foliage. It’s roughly 35 miles long and crests at 2,855 feet.   There are several awesome vista stops, twist and turns and even a switchback. We take another narrow notch road back to our or hotel.
  • Day 5 – Today will be perhaps our longest riding, close to 285 miles if we ride the entire route. The mission here is to get a sense of some of the beautiful forested lake country that Maine has to offer. We will ride a big loop heading north that takes us up to Rangeley Lake via the scenic byway of the same name. This lake is nestled in the midst of thousands of acres of Maine forest. It has a very active hiking, hunting and watersports scene going on. After we stop to visit and enjoy lunch we loop back down south through Fryeburg Maine into New Hampshire, working our way close to Ossipee Lake before finding our way to our classic lakeside inn at Wolfeboro on Lake Winnipesaukee.
  • Day 6 – It’s all about the lake today. After our long ride yesterday today will be a mellow day where you can spend some time enjoying the town, riding, or both. Lake Winnipesaukee is approx 21 miles long, the largest lake in New Hampshire and the 3rd largest lake in New England. It is also a major tourist destination. Wolfeboro is a fantastic little town to hang out in, take a boat ride and people watch. The famous Castle in the Clouds is a short ride away. The ride around the lake itself is a lot of fun with numerous vistas and places to stop. Other well-know beautiful lakeside towns include Merideth and Alton Bay. There is also Wiers Beach, the epicenter of the annual NH Bike week event. Our ride will includes these cool places as well as some elevated roads providing awesome views of the lake.
  • Day 7 – The goal today is to give you a taste of the beautiful and unique New England coast. Maine of course is famous for its coast. NH only has approx 13 miles of coast, but you get to see how impressive it is. First we have to get to the coast, so we cut over through some scenic NH back roads and into Maine, where we come out on the ocean coast at Kennebunport. This town is frequently ranked as one of the prettiest coastal towns in all of Maine, but then again so are one or two other we will visit as we head south. This ride is all about enjoying the scenery and viewing the special vibe that is the New england coast. We stick as close to the water as we can riding through several classic coastal towns while enjoying both the sandy beaches and rocky shoreline that make up this region. You can even have “Lobsta” at our oceanside lunch. We thread our way through Portsmouth NH, along New Hampshire’s stunning coast and end the day at our historic inn in Hampton. If you like today you will almost certainly want to come back for the Maine Coast Wander tour.
  • Day 8 – We wrap up a great tour with a group breakfast, say our farewells, until the next tour 🙂 to our new found friends and then head back home or onto to our next rides.


  • If you would like to come sooner, or stay longer, hotel arrangements can readily be made to suit your schedule.
  • When to book your reservation obviously depends on your schedule. As a rule I suggest at least 3 months in advance to ensure that we can book the rooms you want and to secure a place on the tour. We are staying at some of the most sought after hotels and inns in the most desireable locations – so sooner is better. There is a limit of 7 motorcycles or 10 people, whichever comes first, per tour. 
  • The final cut-off date is technically 30 days before the tour starts.  If someone contacts me to sign up with less than 30 days to go every effort will be made to accommodate you.


5 riders or 7 Tour Members


Please “Contact Me” by telephone or e-mail to book your spot on this tour. I am not a paperwork intensive person. So, the process of making a reservation and getting what I need for my records is pretty simple.

Feel free to contact me to ask any questions about my tours. If I can be of help in any way I’ll be glad to do so.

Final Thought – This tour will give you a taste for some of the Best of the Best that New England has to offer. That is true for the roads we ride, the towns we stay in and the classic historical lodgings we rest and dine at. You might even wind up determined to move here – it’s happened before.