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Hi everyone,
I'm planning a ride starting from New York City, heading north to Maine, then west to Buffalo. From here I'd go East to Albany through the finger lakes, and finally back to NYC, stopping at the Catskills and a few towns along the Hudson. I'll mostly be couch surfing and camping along the way except for a few places that I have friends and family. The trip will be about a year from now, but the trip is a relatively long one for me so I figured I'd start planning now. The ideal length for the trip is between four and five weeks from mid-May until mid- or late-June, so keep that in mind to let me know if I should cut some places. Might be able to sneak in a sixth week, but the goal is really to be back in the City by the start of July. As far as what to do in each place, I think I'll be ok planning it myself, just trying to see the feasibility of the trip itself. That being said, I'd be open to revisions if something to see or do comes highly recommended. I'll get into more specifics here:

Leg One: This is based on a New England Road trip that I found posted online so please let me know if this (or any other part of my trip for that matter) is unfeasible. For this leg, it seems that most drives are under 2 hours.
- NYC to New Haven: stay in New Haven for one day
- New Haven to Newport: Stay in Newport for one day
- Newport to Cape Cod: Stay in Cape Cod for two days. Trying to make it out to Nantucket and/or Martha's.
- Cape Cod to Boston: stay in Boston for three days. I'll be staying with friends here so no need to camp. Definitely trying to hit up some museums and monuments of course.
- Boston to Portsmouth: stay in Portsmouth for one day.
- Portsmouth to Portland: Stay in Portland for one day.
- Portland to Acadia National Park: stay in Acadia for three days. I've always wanted to come here so in a way, this whole trip is an excuse to ride out here. I imagine I'll have little trouble camping here. If you have any recommendations for towns just outside the park that I can either go see in a couple hours or get some lunch please let me know (not crucial though).
-Acadia National Park to White Mountain National Forest: Stay in white mountain 2 days. At about 5.5 hours, this is definitely the longest ride I'm taking. If you know any towns between these two that you recommend in order to cut it down, I'm all ears.
- White Mountain to Burlington: stay in Burlington 2 days.

Leg Two: here's a stint in Upstate New York on my round-about way back home.
- Burlington to the Adirondacks: stay in the Adirondacks for two days
- Adirondacks to Syracuse: stay in Syracuse for two days
- Syracuse to Rochester: stay in Rochester two days
- Rochester to Buffalo: stay in Buffalo two days. here I'll definitely make a trip out to the Falls.
- Buffalo to Albany: This is the part that I do need help planning. I'm trying to see the Finger Lakes area and cover this in about 5 days. Let me know if you know any nice towns or places to camp. I'd like one day to see Albany, maybe two if you think its necessary.
Albany to the Catskills: stay in the Catskills for two days.
Catskills to NYC: Hoping to make this over the course of four or five days. Also not sure what towns to hit but I'm deciding between kingston, New paltz, Beacon, Newburgh, Cold Spring, and Piermont. Open to suggestions of course!

Thanks for taking the time to read this long entry and thanks in advance for any advice!
 

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Sounds like a great trip! Whole bunch of good stops not sure what you are looking to do at some of these stops. I live near your last stop and been to all of the listed stops in the Hudson Valley but based on your being from NYC you likely have been to many as well. Mohonk Mt may be something to add to the list if you enjoy hiking and or rock scrambling. Bear Mt State park would be another place to stop but you have likely be there already Wed nights during the summer they usually have a car show with a very large turn out it may be a fun night to stop by. Newburgh doesn't have much except the water front restaurants the is a place called Billy Joe's Rib works most weekends the have a decent amount of Bikers show up that and boaters (I usually go by boat) The food is OK not great.
Cold Spring is another tourist town a lot of people come by both bike and again boats because it is a waterfront town. Once again Kingston is yet another nice town lots of bikers and yes you guessed it boaters. All of these towns are old towns with lots of window shopping to do. Not sure if you are bringing a wife I know my wife enjoys walking all of these towns and grabbing a bit to eat. Another nice walk would Poughkeepsie the old bridge turned into the walk across the Hudson. All of the above are one day sights or simply a nice place to stop for a rest along your way.
Even though it is a year away enjoy the planning stage!
 

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NYC to New Haven on Route 15 (known as the Merit Pkwy in CT) .........stay in North Haven. (Call me and we’ll have dinner!!)

From. North Haven.......Route 5 to Route 22 to Route 77or 79 (either) to Route 1 to Rhode Island to Jamestown/Newport Bridge (two separate bridges).

You will cross the Jamestown Bridge first. Stay in Jamestown (cheaper; friendlier folks). Drive into Newport the next morning. (Newport Bridge will cost you......Toll)

Avoid Route 6 in or out of Cape Cod at high volume hours. Only way in or out, btw..
 
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