Rolling Thru Maine: September 25 – 28, 2019

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Maine! Imagine feeling the gentle sea breeze off the Atlantic as we guide you along the smooth rolling roads that touch along Maine’s spectacular seashore… Visiting majestic lighthouses, stopping in quaint coastal villages, and riding through Maine’s gorgeous forests… Cruising Maine’s lake district along the foothills of Maine’s mountain ranges… Calling a classic Maine coastal town your home-away-from-home for 3 amazing days. And, those are only SOME of the highlights!


Package: $569.00 per person

Aerial view of Camden, Maine harbor in fall


Lodging: $657.00 per double occupancy room
*Tax and Gratuity is included in above pricing

September 25 – 28, 2019

Click here to sign up!

Wednesday – Welcome to Maine!
You’ll stay in one of the most beautiful, ocean-side resorts in Maine known as one of the finest luxury resorts in New England. The Samoset Resort is a five-star property perched on 230 waterfront acres overlooking Penobscot Bay and will be your gorgeous home away from home.IMG_7436

Your hotel is located near Rockland, a charming ocean-side village with restaurants, shops and a harbor full of classic Atlantic schooners.

When you check in, your Rolling Thru Maine representative will be there to facilitate the process and make sure everything goes smoothly. You’ll receive your Rolling Thru Maine package, with credentials, route maps (in case you decide to ride on your own), and your special gift.

resort-5Freshen up, walk along the waterfront, or discover the resort’s own lighthouse, then come and join us at the Rolling Thru Maine Welcome cocktail and dinner. It’s a perfect time to make new friends as well as meet your tour guides, and hear about the highlights of the upcoming adventure. Best of all, we’ve put together one heck of a dinner: Seafood Chowder, New England Baked Haddock, Sauteed Breast of Chicken Marsala, Marinated Flank Steak

Thursday – Lighthouses and Coastal Riding – Approx 160 miles: 

Lighthouse on a Rocky Coastline

Get ready for a great day of riding following a great breakfast. We’ve created the ideal route taking you along one of the most scenic coastal routes on the east coast. Have your camera ready, because we’ll guide you along winding peninsula roads, periodically riding along the seaside, passing by and visiting lighthouses along the way. You’ll enjoy the newly paved roads Maine has to offer.


Riding along bays and coves, through peninsulas, and past picturesque fishing villages, you’ll arrive at a fun, out of the way, ocean-side restaurant for a fabulous meal. Directly overlooking the ocean, with fantastic views, you’ll feast on Seafood Newburg w/lobster, shrimp, and haddock, Roast Boneless Pork Loin w/Port wine demi-glace, Grilled Chicken w/creamy pesto and more.

Curving scenic road in Acadia National ParkAfterward, we’ll stop in one of the most picturesque fishing villages in the state, giving you an opportunity to enjoy the unique and wonderful atmosphere unique to Maine. Shop, walk along the fishing piers and enjoy a Maine Whoopie Pie (so good, there’s a fan website for them). When we return to the hotel, you’ll have the evening to yourself. Enjoy a dinner at one of the 4 restaurants at the hotel or if you prefer to choose from the many restaurants nearby Rockland has to offer.

Rockport Harbor

Friday – Fishing Villages, Lighthouses, and Mountaintops – Approx 135 miles: Marshall Point Lighthouse
Today’s route, following another great breakfast, is a mix of land and seacoast. From a quaint fisherman village to a mountaintop with a breathtaking view, this day will surely please you. We’ll start the day with a quick stop at the transportation museum. We’ll then take you to the famous Marshall Lighthouse seen in the movie Forrest Gump.

Harbor with rustic fishing shack and pier in MaineFrom there you’ll ride along the seacoast overlooking Penobscot Bay, stopping for lunch at an amazing mountain top lunch venue. You’ll enjoy a spectacular view overlooking the ocean while feasting on a delicious meal including Roasted Salmon w/Chives Butter, Petit Filet of Beef w/Roasted Shallot Demi-Glace and more.

After lunch, you’ll ride inland on smooth, winding roads with a stop at a local Vineyard.

At the hotel, you’re invited for a cocktail followed by another delicious meal with the company of your new and old friends. The menu includes Chicken Saltimbocca, Shrimp Scampi, Pork Puttanesca, and Spinach 3 cheese cannelloni. What a day!

Saturday – See you Next Year!
A special Farewell Breakfast awaits you. You’ll say goodbye to new and old friends, see photos from the trip, and will likely be thinking about your next Rolling Thru America tour.  

Coastal Road - Maine

Photo credits include the Topside Inn.

25 thoughts on “Rolling Thru Maine: September 25 – 28, 2019

    1. Hi Laurie,

      For 2 people to attend and stay in 1 room, this would be the pricing. All packages come with 3 breakfasts, 2 lunches, and 2 dinners and all entry fees into anything we have planned. You are only responsible for gas, 1 dinner, and your souvenirs.

      Package: $569/person x 2 people = $1,138.00
      Lodging for 3 nights for 2 people in 1 room: $657.00
      Total cost: $1,795.00

      We hope you can join us!



    1. Hi Robin,

      It’s a great ride with fantastic scenery, a gorgeous hotel, delicious meals, and awesome riding. We hope you can join us!

      Please let me know any questions!


    1. Hi David,

      We understand. Different riders want different distances and experiences. Our tours have been hugely popular (some selling out in 24 hours). Our Maine tour was loved (!) last year, but if you’re looking to log more miles then this may not be for you.

      Also, some of our attendees do arrive a day early, or leave a day later, to soak up more riding. Perhaps that could be an option for you.



      1. Hi Charles,

        The total for 2 people, which includes your lodging for 3 nights in a gorgeous hotel, 3 breakfasts, 2 lunches, 2 dinners, guides who lead you on the tour, a souvenier bag, a chase car and more is $1,795

        We have been told our pricing is great compared to other events, where you don’t get nearly what we offer.

        We hope you will give one of our tours a shot sometimes soon1



      2. Charles –
        As a two-event participant, I can tell you that this is a very special rider’s event that you’ll never forget. It may seem pricey, but it’s first-class all the way. I wrote an article for ROADRunner magazine on the first one,” Rolling Thru Vermont”, a few years ago. The e-magazine article can be found on their website, under articles of previous rides. If you’re a “mature rider” (as am I), I would strongly encourage you to go for it. You won’t be sorry. Hope to see you there.

        Gary ‘Wildman” Winn


      3. Where else can you ride with “like minded” responsible rider’s like yourself, that enjoy motorcycle riding to it’s fullest?
        Enjoy great foods, sleep in high class motels, see area’s that many have never seen before…I’m in!

        Ronnie McClements
        Springfield, Massachusetts


    2. Hi David. I noticed your response and can tell you that, as a Riding-Thru participant X 2, this riding event is all about quality, not maybe quantity. When you can stop every so often to check out some really neat scenery, and mix with motorcyclists of your caliber, it’s very cool, and should be experienced. “Riding-Thru” events aren’t for everybody, but I’ve found them to be a most memorable chapter in my up-coming book, “My Life on a Bike -What a Ride!” Come along if it’s not sold out.


  1. I live in Miami Florida, where would be a good airport that would be close to a Harley or eagle rider store to rent a softail
    Or trike


    1. Hi Charles,

      The price for a couple in 1 room would be as follows:

      Package: $569/person = $1,138.00
      Hotel for 3 nights(2 people in 1 room) – $657.00
      Total – $1,795.00

      Please let me know any other questions!


  2. I want to go but I will be riding single as my wife does have to work during those dates (She works for the school dept./so time off can not happen)


  3. I didn’t finish my question here sorry! Will it be any cheaper for a single rider, that will be staying alone instead of two


    1. Hi Ronald,

      Here is the pricing for 1 person and the hotel room with 1 person in it: Package $569 + Lodging $657 = $1,226
      Here is the pricing for 2 people and the hotel room with 2 people in it: Package $1,138 + Lodging $657 = $1,795

      Have a great day!


  4. HI Ronald,

    We are working on having the itinerary emailed out in the next week. Addresses and GPX files will be a week out of the event. See you soon!



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