Have planned our group rides using the above site for years. Once you have set your objectives, look at this site for the great roads to from, and around your key destinations.

That said, have ridden to or thru most of the various places mentioned in this thread. A lot of great ones. A real lot.

Planning a trip is always a difficult blend of interests, riding styles, included and dismissed destinations. As with many places, the subject area is vast, and you can't do it all.

Our group trips last 7-9 days. We have done about 5 separate dedicated trips within the area discussed, plus have multiple houses at Laconia every year, and tour NH and ME from there, We have not done or seen all.

Most recently, we went to Hunter Mountain for the zip line, West Point, long haul to Gettysburg, back thru PA, into NYC for the 911 Memorial and Freedom Tower. Prior to that, Portland ME to Nova Scotia by ferry (not available this year) to the Cabot Trail, Halifax, Oak Island, and coastal touring. Year before that, up to Burlington VT, into Hero to the boarder, Ausable Chasm, Lake Placid, Lake George, Catskills. Year before that , Sturgis. We still have sites to see and roads we want to ride. This year, we are going to Portland, then Arcadia for 5 days, and back down the coast for two more, Old Orchard or Hampton Beach TBD.

My point is, the area is vast. Try and figure out your interests and important inclusions. IT's your trip ! Once you have identified your main targets, post them up, and you will get better help finding the best ways to tour thru "our" area ! Style of riding will help too. Some are Iron Butt types, others only go long a couple of days. Food important ? What types ? T-shirt collector ? Biker bars important ? Have you noticed everybody mentioned Bentley's ? There are others. Sea coast riding ? Some great roads from Hampton Beach NH to Ogunquit ME. Mountain climbing rides, Whiteface in NY is an awesome easy ride. Mt Washington in NH more of a challenge.

Good Luck !

 

Never a more important statement said about touring ! Time to ride the destination is vital.

I live near Mom's, and have only good things to say about them. However, as a suggestion, check out Boston Harley as a rental site. Not far from Logan Airport in Boston. Same true of Manchester NH Harley from Manchester Airport. But, I am not sure they rent bikes.

 

We have been shipping our bike, then flying to our destination. Financially it makes sense right round the time you have rented a bike for about 7 days. So for us, if it is a 10 day or two week trip, cheaper to ship our bike, and I would much rather ride my bike anyway.

Two years ago we spent 9 days riding to Sturgis, then 7 days in Sturgis with friends in a rented house. Decided to ship the bike home, and we flew. Our house mates had only made it to Sioux Falls by dinner time, we were safe and sound back on the Island for dinner. They took three days with trucks and trailers. Just a thought.

PS the wife and I enjoyed the 9 days to Sturgis, living on the road over the 7 days in Sturgis.