How much time do you have for this trip?

I have no particular time limit.

The first 2 weeks of October are very popular so make reservations early in NH and VT. You can get wine trail maps for the different states. This might help you plan where you would like to go. For example, last summer we visited a winery in Rockland ME and then another more inland. Cellar Door Winery is also close to that area.

I don't think you have time for Canada if you have all those interests. Here's some scattered ideas:
Hiking - any place in the White Mountains of NH but remember to dress appropriately for weather that may go from 70 to freezing. Last summer we got a map to trails in the Harpswell area of Maine (go east from Brunswick). There are some conservation areas that are open and can be short, easy hikes. Brunswick is a college town so you should fine some good beer, music, etc.

Portland ME is considered one of the foodiest towns in the US. The Old Port Area is a lot of fun. It includes a brewery you can tour. Duckfat has interesting and delicious fries. Check out the farmers market schedule. You can take a foodie tour of this area and get small samples at several stops. Don't miss MDI ice cream - get the sampler after requesting a couple of tastes. I don't care for Wasabi Chocolate but you might.

Chowhound is a great resource for restaruant recommendations. Read thru old posts. Just put in a city name in the Northern New England section.

Boston has two great food tours I've been on: the Italian North End and Chinatown. The Chinatown one ends with a dim sum lunch so it's nice to be in a group.

If the weather is good, you might still be able to go kayaking in various locations. There are rental places on both rivers and ocean. Will probably be weekends only in October.

A boat trip to Monhegan Island would also provide fun hiking if weather is good. Bring your own picnic lunch. Don't forget the binnoculars.

Portland - Portsmouth NH - Boston - Newport RI would give you a great coastal tour.

There will be foliage festivals on Columbus Day weekend. The free Hippo Press gives a great listing of wine and beer events in the Nashua/Concord/Manchester/Portsmouth NH area. See their website. Would also be a good resource for music and other events.

VT: since you are interested in healthy food, you might like to read The Town That Food Saved which is about Hardwick VT. Brattleboro VT has one of the best farmers markets in the state. You can get an ethnic lunch there. Not sure when they close for the season. Also check out the lunch truck in downtown which serves some great bahn mi sandwiches. They might still be there in early October. It's a funky town I'd like to explore more. The lunch truck is in Harmony Parking Lot but darn, can't remember the name of the truck. They have a facebook page. Brattleboro VT is not far across the river from Keene NH which is a nice college town.

Burlington VT at the northern end of the state would also be a fun visit. Also a college town on beautiful Lake Champlain.

I would also check the different Audubon groups in the various states. Here's a link to info about the fall hawk migration http://www.nhaudubon.org/locations/raptor-observatories
One site is near Concord NH which is a nice small city. The Concord Food Coop has a small cafe serving healthy food. Usually free wine tastings each Thurs night at Butters. You won't have trouble finding unique beers. Red River Theater is a small independent theater and next door Gibson's bookstore frequently hosts authors. Just check the schedule near your visit. You might find an author or film that interests you. Sometimes Red River has films plus discussions. The Barley House is a popular bar/restaurant.

This is just a quick list but I hope it explains why I don't think you have time for Canada.

Hopefully someone else can help you with fishing and sports.

Everything dfrostnh says plus Burlington, VT, which has great beer and music scenes and is within daytrip or overnight of Montreal.

Early October it is really beautiful in NE and really crowded. My sister and I had to cut short a trip because we could not find lodging anywhere within 50 miles of Stow/Montpelier. Columbus Day is a major holiday in NE, so you pretty much have to have reservations.

Hiking in NE is wonderful but may be very different from where you are coming from, and the weather is not likely to be better. You are likely to run into snow at higher elevations, and Mt Washington famously has "the worst weather in North America." This can actually be a good challenge, but you cannot hike in jeans/cotton hoodies/etc. And many trails are generally much rougher and narrower than in the west. Don't go without appropriate gear and sturdy -- that's sturdy -- hiking boots. There are rewarding "walks in the woods" in many places -- Mt Chocorua, NH, on the Champney Trail from the north and Mt Willard in Crawford Notch immediately come to mind -- but summiting Mount Washington from the Base Station in Bretton Woods or from Pinkham Notch requires more gear and preparation.

VT now has more craft breweries per capita than any other state. If you are coming through north central VT, Three Penny in Montpelier and Prohibition Pig are good places to visit for a big selection.
Try some Heady Topper from the Alchemist brewery in Waterbury

Lots of good hiking along the Long Trail in Vt. As others have noted, it can be very cold in October although the weather is not as extreme as that in the White Mts in New Hampshire described in the last post.

I would suggest going to Montreal and maybe exploring the wine and/or cider routes in the Eastern Townships of Quebec.

Ylu can xrive up to Montreal after northern VT since you have no time restraints. Cross over to NY State to access the interstate.

I can't believe the OP is totally dissing Rhode Island. ;^)

Anyone else?

Oh, and thank you everyone that contributed

If you have no particular time constraints you could do a long loop through New England. If you start in Boston you can drive up to Portland (about 1.5 hours) and get some amazing lobster. Next drive up to Acadia NP (about 3 hours). Spend a few days in Maine and hike, bike, fish, eat in Acadia or anywhere else. Next you should drive from Acadia across Main to the White Mountains and do a hike on one of the mountains. Remember, mountain weather is ridiculously unpredictable, I was hiking up a relatively small mountain (3,000 ft) in April and it was in the upper 60's at the bottom and snowing at the top. Another 1,000-2,000 feet and it would have been a full on blizzard. I recommend you stay in North Conway but instead of continuing on 95 South until route 122 get off of 95 at 202 and go through Paris, Norway, and Bethel, ME. If you are in Bethel, ME for the night I recommend staying at the Chapman Inn, the owner cooks cinnamon rolls and muffins every morning at 5 am. From Bethel continue on Route 2 until Gorham, NH when you turn south on Route 16. From there to North Conway you will pass Mt madison, adams, jefferson, washington, eisenhower, and mt jackson in that order. Spend however long you want there and then continue on to northern Vermont. Northern VT wil be in full foliage at that time and Kingdom and Victory State Forests are great. If you want to you can stay at what I believe is the best ski resort in the east, Jay Peak, they are open all year round and have concerts, golf courses, tram rides, and even the coolest indoor waterpark at a ski resort that I have ever been to. They have everything including amazing food. The drive is between 2 and 3 hours from North Conway to Jay, VT. From there you will cross a small border crossing a few miles from Jay and it will be about 2 hours to Montreal. Spend however long you want there and then head back to the states. Now is the big question, have you ever been to Lake Placid? If you have then from Montreal continue south and head to Burlington, VT. From there you can drive south on Route 7 to Rutland and then the Berkshires. There are great places in the Berkshires like Mt Greylock and Lenox. Spend a day or two there and head back to Boston using Route 2 from North Adams to I-95. Take a break to see the state forests around the Quabbin Reservoir and do some fishing on the way back. Spend three or four days in Boston and fly or drive back to wherever you are returning to. If you have not seen Lake Placid than I think you should definitely do it. The Olympic Museum, Bobsled track, and Ski Jumping Complex are amazing. Use I-87 from Montreal and turn off at Plattsburgh. There are some great hiking trails and fishing areas in the Adirondacks and you could easily spend 5 days if you really wanted to. I would recommend 3 days in the Adirondacks, 1 for olympic stuff, another 2 for outdoors enjoyment. Then head back south on I-87 to Albany where you get on I-90 until you hit the Mass border. Take exit 2 on I-90 to Lenox and continue North to Williamstown and North Adams. Follow what I said above. I hope this helped. If you have any other questions I will be glad to answer them.

dshamritsky - can you email me if i give you my email? I have very specific questions. Otherwise, ill take some of the venues you mentioned and work them in, but its going to be difficult to follow this route because i was going to use a GPS

Can you list out the cities/states in the order of suggested travel too?

If you are doing Jay peak and don't want to stay at the resort you can always stay nearby at the Phineas Swann Inn in Montgomery Center

The last post says <<Northern VT wil be in full foliage at that time and Kingdom and Victory State Forests are great. >>
I am not sure exactly what time frame this post is suggesting, but it seems that starting in Boston and going to Maine and NH first would put you in northeastern VT in the second week in October at the earliest. Peak foliage in the Northeast Kingdom is generally the end of September/first week of October, although this obviously varies from year to year.

I'd like to recommend a good road map to go with the GPS. If you do some exploring and get on back roads, the GPS can give you bad directions. Not always, just sometimes. We've had visitors directed onto discontinued roads.

I agree with VT that foliage in the north would be past peak by second week. It might not matter but I think heading north first would be best.

Ditto dfrostnh.

We traveled with friends to the Northeast Kingdom this summer, and their normally-ok GPS failed several times. Once it put them on the same-named road, but in the wrong town, other times it couldn't pin-point an address within a half-mile, in another case it made them turn right and drive 2 miles to get to an interstate, while we (separate cars at that point) turned left and got there in 500 yards.

It got even more sketchy in Canada. They ended up turning it off.

Same issue with mobile phones. My traveling companion had set up an over-the-border calling plan so that she would not have to pay outrageous out of country digital roaming charges.

BUT when we got near the border and she tried to activate it, she couldn't get a cellphone signal! And we were still in the US! Cellphone coverage can be very spotty in northern Vermont and NH.

Sorry about the slipup with the foliage, it seemed to slip past my brain that it would be mid october by then. I guess that they would see enough foliage just driving around the white mountains and maine.

Your suggested route is a good one and the OP might not be interested in looking at leaves. You are right, there's going to be plenty of foliage in other places.

Forgot to mention another "sport" - some of the ski areas have mountain bike trails for use during the off season or you can go to a dedicated mountain bike park (there's one somewhat near Lake Winnipesaukee in NH)

Please take a map. We were in Vermont Oct 6 - Oct 13. The road from our resort to Stowe was scheduled to close anytime. GPS would not have knowledge of this and would send you down a road that you would ultimately have to turn around on and spend 2 hours to get where you initially wanted to go.

A point of reference for the foliage. We stayed near Burlington. The foliage was great for the first 2 days and then it all started to fall. By the end of the week many of the trees were bare or lacking color.