I haven't been to Montreal or Burlington in a long, long time so I will skip to the Boston part. I live in the Boston suburbs and find Boston to be frenetic in September. As much as I love the city it kind of drives me crazy - so many college kids back to school, everyone else back to work. etc. etc. The Cape and the islands, on the other hand, are blissful that time of year (assuming you aren't visiting Labor Day weekend!). We have a second home on the Cape and love, love, love the fall here. It is wedding season so weekend accommodations could still be tricky on the Cape/islands but mid-week should be easier. On the Cape, the lower Cape (near the National Seashore) is really nice in the fall and we love the Wequassett resort in Harwich (near Chatham). Nantucket can be visited pretty easily without a car, but accommodations can still be hard in September. For the Vineyard a car is really needed so if you plan a lengthy visit there, you either have to get a car reservation on the ferries or rent a car when you get on the island. Both MV and Nantucket can be visited as day trips with the high speed (no car) ferries. If you decide to visit the Cape I would be happy to provide more info. One of my very favorite things to do on the Cape in the fall is the amazing Rail Trail for biking.

In Burlington you must must do rails to trails, a bike ride along alike Champlain and on a narrow scenic causeway that actually juts out into the lake. Easy to rent bikes, and a fairly easy ride. We loved staying in the cottage at quirky little One of a kind Bnb, and for dining I give very high marks to trattoria Delia and American flatbread. There is also the lovely estate/museum but we didn't get there. If you do, you need 2 full days in Burlington ... If not, one IMHO.

I don't go places twice, so is ditch Boston. Esp since Sept is, IMHO, the perfect time to go to the cape.You are off season for the cape so I think you'll be fine. Where do you fly home from? I'd go to MV if I were you. Can't help you w hotels on MV or Nantucket because we've only rented.

Funny I was typing while Marinagal was and our replies are so similar.

There is another great riverside rails to trails In williamstown, MA, and a very cool museum, mass MOCA, and another favorite, Bnb, Porches. But it'd be a tad out of your way.

Sorry if I seem bike obsessed but it will be a fabulous time of yr to do it and all of these trails are paved, easy, scenic, pristine, and have rentals.including the cape cod one that Marinagal mentioned

Thanks, marina and mtn; I'm already researching your suggestions. So maybe a night in Burlington and then continue on to the Cape. Should we stay on MV if possible, or would it be better to stay on the Cape and do day trips to the island(s)?

We haven't yet purchased our return flight, so we can fly home from anywhere.

We do enjoy cycling, so the bike trails sound great!

One of a Kind B&B looks lovely but us full on 9/10. Darn!

You might want to ask this on the New England forum as there are a couple of folks who live on the Cape.

Here is a link that might be useful: New England forum

On the way from Burlington to Boston (or the Cape), if you like historic sites, consider stopping at Canterbury Shaker Village, just north of Concord, NH, and at Strawbery Banke in Porstmouth, NH.

Portsmouth is a little out of your way, but S B alone is worth it -- a village of preserved and restored buildings, dating from the 1600s through the 1800s. Lots of interesting things to see! Portsmouth itself is fun to walk around in, with other house museums, including the John Paul Jones house, plus interesting shops and restaurants.

If you haven't been to a Shaker village, Canterbury is a very pleasant introduction to their architecture and way of life, with lots to explore.

Here is a link that might be useful: Strawbery Banke

Just a quick note to say it's about 4-4.5 hours from Boston to Burlington VT so I am pretty sure Montreal-Boston is more than 5 hours (I've never driven it myself).

You could also find a lot to do if you stuck to Burlington (a great place) and maybe Maine/NH -- Portland is a great city, and Ogunquit and Kennebunkport would be beautiful in Sept., then Portsmouth.

Rockport, MA is lovely, too. And Newburyport!

Thanks, chibimimi and sue. We've pondered the idea of sticking to Vermont and New Hampshire since both states are new to us. I'll check out the places you mentioned.

We don't have any sort of agenda. On these annual September trips we like driving around and exploring charming areas, a bit of history, a little cycling or hiking, shopping and eating!

We certainly don't have to go as far as Boston but we we're wondering if the Cape/islands are a "must experience." I imagine that while each Eastern port has it's own personality, they're somewhat similar, yes? We've spent time in Nova Scotia and Maine but nothing SW of Rockland.

If it were me, and given you've seen maine, I'd do Burlington and Martha's Vineyard. To me MV is very distinctive

I think the trip from Montreal to Boston could be done in 5 hours -- but only if you don't hit traffic when you get outside Boston; that's where it usually gets wrapped around the axle. Up to that point the roads are great and (comparatively) lightly traveled. So if you can avoid actually going into or too close to Boston, you'll make good time.

I like Burlington well enough, but think there might be more typically-New-England places to visit, especially if you haven't been to VT/NH before. Woodstock, VT, is very charming (if a little touristy), with lots of art galleries and a great country store. There are some wonderful countryside walks, and Quechee Gorge is nearby.

Portsmouth is one of my personal favorites, for the reasons given in the previous post.

Or you could just go straight to Martha's Vineyard and spend all the time there. If you decide to do this and have a little time along the way, get off the interstates here and there to take a parallel road through some of the small towns along the way. Most of the old ones have the quintessential New England white clapboard town hall, Congregational church, and library clustered around a little green. Good photo ops!

Whatever you do, book your rooms now. You're getting close to leaf-peeper season. It really kicks off in October, but bookings start getting tight in late September.

This post was edited by Chibimimi on Sun, Aug 17, 14 at 15:55

You said you are staying downtown in Montreal, do you need restaurant recommendations? best coffee? shopping, etc..

We flew to Montreal, stayed in the Chateau Champlain and enjoyed exploring Old Montreal-great restaurants and sight seeing. In downtown we took a horse buggy ride at night and it was lovely. They provide you with blankets if it's chilly.

I don't think you need more than a day in Burlington. After that, you could head down to Shelburne (Shelburne Museum), Stow, Woodstock and Quechee (Simon Pearce Factory and restaurant-glass blowing).

Even though you have been to Boston, I would suggest a stop. There is a whole new area, the Seaport, which is full of wonderful restaurants. The city has changed so much in the last few years.

From Boston head to the Cape. Stop in Plymoth is you have never been. You can stay on the Cape and take day trips to the islands. You can take a Freedom Cruise Ferry from Harwich Port to Nantucket. It's only 80 minutes and you can park free at the lot. In Nantucket I highly recommend the Union Street Inn (if you decide to stay overnight). It's a lovely B&B.

Definitely go to Martha's Vineyard. You can take the car on the ferry from Wood's Hole or from Hyannis. You might want to spend a night on the Vineyard. Renting bikes is a fun way to see parts of the island.

Septemeber is shoulder season on the Cape/Islands. Schools are back in session, weedays will be quieter, weekends busy. You should not have difficulty finding mid-week reservations at this point. Rent bikes and ride the Cape Cod Rail Trail. You can stop along the way for breakfast or lunch.

We have a house on the Cape, and have beeing going there for years. Plan on meandering along Route 6A (on the North side-the bay side) by car. It's scenic and will give you a good sense of the various towns and their history.

I'm happy to make recommendations for restaurants, activities, etc. Have fun planning!

You can fly home from Providence or Boston.

Sure mitchdesj, I'd love restaurant recommendations in Montreal. A favorite or two would be fine. My go to for recommendations is tripadvisor in combination with the concierge. bonnie, I'd love to do a carriage ride but my husband sneezes the whole time, making the experience quite unromantic. :)

I appreciate all the suggestions. I'm still trying to fit all the puzzle pieces together for a cross-international border rental car drop and hotel availability, but we're leaning toward departing Montreal very early, stopping in Burlington and a couple other places stated above and staying where we're lead that night. We'll head for MV the next day.

Would you all recommend staying right in Oak Bluffs on MV? Should we experience anything in particular on Cape Cod?

Thanks again!

I live on Cape Cod and can tell you that, the absolute best month of the year on Cape Cod is September. It tends to be warm enough for touring and swimming, but cool at night for sleeping. Plus, the summer crowds are gone.

Hyannis is pretty pukey. The Outer Cape is beautiful, namely Truro and Provincetown, and Ptown is a happening, hopping town with very colorful people and great restaurants.

Chatham is also a beautiful (expensive) town. The National Seashore, which runs from Eastham to Ptown, is gorgeous.

If you want to get around all of the Cape and Islands in a few days, try to find a rental that is centrally located, i.e.: "MidCape".

Look on weneedavacation.com and homeaway.com/vrbo.com (these are the two sites where I advertise my house). Labor Day Weekend will be tough to find a rental.

I hope you see the cathedral while in Montreal. I spent a day there with friends familiar with it all and while we drove/walked around and saw the highlights, the cathedral was by far my favorite part ( although the Olympic stadium dome was really interesting)

jujubean

I live in Montreal, and it sounds like you already have a place picked out to stay in the downtown area.

So here are a few of my favorite nice restaurants.

On a very typical french street and area in Montreal there is this little Bistro with great food on Rue St.Denis.

http://www.restaurantlexpress.ca/m/en/

Then there is a place called Joe Beef which is always a good and hearty meal.This is in the downtown area.

http://www.joebeef.ca/

and last there is a quaint street in the Outremont area which is very much like spending a day in Paris.It is called Laurier street and I love going there.
Small Boutique like shops, a nice smallish grocery called VanHoutte with fine delacasies from other countries but mostly France. Unbelievlably good cheeses and other fine things
.A nice place for lunch or dinner if you do go to Laurier Street is Lemeac

http://restaurantlemeac.com/

I am not sure where you are staying but I would venture to guess that most of these places are a 10.00 cab ride from any downtown hotels.

Have a good time. I see this is a mixed buisness trip for your DH so your evenings might be planned but if you have free time to fill I would do either Rue Laurier or Rue St. Denis on your own in daytime if you need somewhere to go

Yes, Bumblebeez, we will see the cathedral. We generally like to walk around Olympic villages, so thanks for that tip.

Laban, thank you for those recommendations! Noted. I'd very much like to visit Laurier Street. We have an exchange student from France arriving next week, so I'll be sure to pick up something for him from VanHoutte. Fun.

Tibbrix, we are visiting 9 days after Labor Day. I'm going to email you. :)

What a fun and FULL day we had today! We left Montreal bright and early this morning after a great five-night stay and visited Burlington (University of Vermont and Lake Champlain), Waterbury (Ben & Jerry's tour), Montpelier (VT capital), Concord (NH capital), Canterbury Shaker Village, Portsmouth (love, love, LOVE!) and Strawbery Banke, New Castle and the entire NH coast (all 13 miles :), followed by a yummy fish dinner overlooking the ocean near Newburyport and a night drive through beautifully-lit Boston. Now it's time to rest up for a little more history in the morning (Plymouth Rock and the Mayflower) and a few days on Martha's Vineyard and Cape Cod.

Thank you, all, for the suggestions! I love travel days like this that are jam packed with new things to see and do.

We really enjoyed Montreal. Fabulous food at every turn, of course. I've eaten more baguette in a few days than I usually consume in a year. And I found myself missing France with each bite. Loved the pastry school cafe Maison Christian Faure for lunch. Lyban, we shopped on Rue St Denis and Rue Laurier (twice), ate at Lemeac and went to VanHoutte (where I was reprimanded for snapping a photo of the fantastic cheese display - oops). We also got bagels at that well known shop a couple streets to the north, but the name escapes me. We stayed in Old Montreal and walked and walked each day and hopefully saw most things there are to see. Beautiful architecture. Enjoyed a few museums, a couple exhibits, saw a musical at Place de Arts, spent time at Park Royal and McGill University, did a guided bicycle tour of the city (highly recommended - we do this often and it's usually a top memory of a city, as it was this time). We also cycled around the little islands in the river ... St Helen's and ??? . Lovely city. Would return for sure but I've become a smaller town girl with age and liked Quebec City even better.

Glad you enjoyed montreal.
Bagel shop was probably either St. Viateur bagel
Or fairmount bagels.
Aren't they good.
I understand about liking smaller places better, Quebec City is lovely and construction in montreal right now is dreadful.