Planning Fall 2016 trip

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Since I have never been to New England I am planning a10 day so trip Sept/Oct 2016. I am in OR. so will fly to the start and then back home. I have looked at the schedule of train service for New England and I am just lost in trying to come up with an itinerary. I would like a couple of walkable stopovers in smaller towns to really see what New England is like. The only thing on my wish list is maybe the Cardinal Eastbound. I have enough points for a roomette on one leg but the rest will be paid. Any ideas or suggestions will be greatly appreciated.
 
One trip that's really worthwhile is to take the Downeaster from Boston ( North Station) to Portland ,Maine and return. ( there are also Thruway buses to/from Portland but the train is lots better!)

Beautiful old Mill Cities that have been reclaimed and become commuter Towns for Boston,the great little Fishing Town of Portland ( Great Sea Food) and a really well run train ( several Trains daily in each direction) with friendly Maine Crews.

You can also ride the Ethan Allen, the Vermonter and the Adirondack from New York. The ride up the Hudson River and along Lake Champlain is especially pretty, and since it terminates in Montreal, a really great International City,( you need your Passport) you can spend a couple of days enjoying the Canadian and Quebequois Culture!
 
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And although not Amtrak, there are many excursion railroads in Vermont, New Hampshire area that offer some beautiful rides behind steam engines or diesels through the countryside. We did a combined Amtrak and bus tour several years ago that offered a nice 10 day vacation throughout New England.
 
One stop we enjoy is Mystic, CT from the NE Regional. It is a good place to spend a day.
 
Try Brattleboro, VT on the Vermonter route. I grew up in New England, and when I passed thru Brattleboro a few years back, I felt like I was truly in

New England. It's an artsy place, too.

I don't know where you are planning your trip, but a stopover in Old Saybrook, CT or Mystic would get you some seacoast flavor.

There is nothing you can do in terms of a very "coherent" itinerary. When you get to Boston, you can get the Downeaster up to Portland, but then you've got

to come back to Boston and from there, you can go west to Springfield on # 449. There is no valid connection to the Vermonter at Springfield to go north into

Vermont. Connectivity by train in Northern New England has become pretty much extinct.
 
Thanks so much for the suggestions for ME., CN. and the towns to visit. I had planned to ride the Vermonter and the Adirondack, so a stop in Battleboro is an option. I notice there is stop for Burlington on both trains (Essex Jct and Port Kent) but I don't understand the connection, can someone explain it? Also in looking at the Amtrak System Timetable I'm not finding the 449, but I probably overlooked it.

It appears that in putting something together it will mean some back tracking and/or bus connections. At the end maybe the LSL back to Chicago. Thanks again.
 
Train 449 is the Boston section of the Lake Shore Limited. Concerning Burlington: Essex Jct. is next to Burlington, and requires a taxi ride, I believe. There is a ferry from Burlington across Lake Champlain to Port Kent on the New York side. The ferry operates "seasonally", so it's best to call them to see if their operation dovetails with your dates of travel.

If you want a really circuitous routing: Chicago -New York [via Cincinnati]-Boston-Portland ME-Boston-Springfield- Essex Jct.-Burlington-Port Kent-Albany-Springfield-New York-Chicago [via Cleveland]. The only backtracking will be between Portland, ME and Boston. Of course, lack of good connectivity is going to require some overnight stays in hotels, unfortunately. That could be a plus, though. There are some wonderful B&Bs in some of these New England towns.

This will put you up and over the Berkshire Hills in Western MA as well as a very scenic ride up the Hudson River, and if the time of year is right, along the Mohawk River Valley.
 
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It's not really true that you'd have to do an overnight layover if you wanted to get from Maine to Vermont.

Weekdays you could depart Portland (POR) at 5:20am, and arrive at North Station (BON) at 7:50am. You'd have to self-transfer from BON to South Station (BOS) or Back Bay (BBY) to get down to New Haven (NHV) to catch the Vermonter. Following are your connection options, I will leave the connections Amtrak.com offers from POR to NHV, so these will have to transfer between BON and BBY, though you could always go to BOS if you'd prefer.

Depart BBY at 9:20am on Acela 2159, and arrive in NHV at 11:11am. Or depart BBY at 9:36am on Regional 93, and arrive in NHV at 12:04pm.

The Vermonter departs NHV going northbound at 1:25pm. The Acela should certainly be enough time to make the connection, as well as 93 should be a long enough connection. You'd have to weigh out the cost of the Acela vs Regional ticket, and being more likely to make the connection. But nonetheless, same day connections ARE certainly possible from Portland to stops on the Vermonter. Unfortunately, they are not guaranteed by Amtrak.

Edit: Also, I will add my vote for Mystic. Beautiful city, in the right places. Mystic Village is always a great place to visit too!
 
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Thanks so much, this is what I needed to get started with my planning. Stopovers are an important part of the trip and some towns (Mystic 2x) have already been suggested but more are welcome. I have the system timetable and maps but I may have more questions. Living in Oregon I thought flying in and out of Chicago would be best and it looks like that would work. My plan is for Fall before the rush of leaf peepers so lodging will be easier to obtain. Appreciate the connection info for Portland and Boston. Any other suggestions welcome.
 
Thanks so much for the suggestions for ME., CN. and the towns to visit. I had planned to ride the Vermonter and the Adirondack, so a stop in Battleboro is an option. I notice there is stop for Burlington on both trains (Essex Jct and Port Kent) but I don't understand the connection, can someone explain it? Also in looking at the Amtrak System Timetable I'm not finding the 449, but I probably overlooked it.

It appears that in putting something together it will mean some back tracking and/or bus connections. At the end maybe the LSL back to Chicago. Thanks again.
Our family did a trip one year involving the Adirondack, Port Kent Ferry and Vermonter. You might need a Taxi from Essex Jct to the ferry dock. I don't know the transit system in Burlington, and we were renting a car in Burlington.
 
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