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October Road Trip - Need suggestions!!

A friend and I are going to to be taking a road trip from southern Maine down to Connecticut in October. Neither of us have been to the area and are looking for suggestions for everything...where to stay, what to do and, of course, where to eat. Any help is greatly appreciated! Thanks so much!!

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  1. Are you looking for southern Maine recs? Does that include Portland?

    1. What do you like to do? Where are you from? Budget? Where in CT are you driving to?

      1. Sorry, I know my description is vague. We were actually planning to start in Portland. We're not really sure where in Connecticut we're planning to drive to. Like I said, neither of us have ever been anywhere around there, so we have no idea what area are good to go to.

        Our budget is fairly flexible. We'd probably tend to stay away from too many high-end activities/restaurants (we're both teachers :), but a splurge or two is certainly doable.

        2 Replies
        1. re: raeberak37

          Early October, as in leaf peeping?

          Shopping? As in going to outlets?

          Historical sites?

          Depending on what your interested in you will get different answers.

          Generally speaking leaf peeping peaks around mid-October. For foliage you would be best served going inland towards NH, VT, western MA and western CT.

          If you want to see historical sites Boston is where you want to go. Which is the opposite direction for leaf peeping.

          A place you may not have considered is Newport, RI? Beautiful seaport that is where the Vanderbilt's "summered", they built some very impressive cottages you can tour.

          October is high season in Salem, MA. Witch trials and all that haloweeny stuff.

          Of course the Red Sox will be in the playoffs.

          In Maine the place for shopping is Freeport, about 30-45 minute drive north of Portland. The most famous retailer being LL Bean. Kittery is the other shopping destination in Maine.

          Need further guidance to get much more specific. Just be aware that fall is peak season in New England. If you have any specific lodging in mind I'd be making a reservation.

          1. re: raeberak37

            Depending on when you go in October may dictate your route. That time of year, I'd probably be chasing the leaves, finding the best color and best vistas. Most small towns in New England will do, especially when you stick to our back roads :). I personally love the White Mt. and Lakes Regions in NH for fall color. If the leaves aren't good when you come, you may want to just stick to a Seacoast route. If you do that, a great area is Portsmouth and Rye, NH. My fav seafood spot being Petey's, right across from the beach in Rye.

            I don't have any favorites in MA, but I would think travels through Boston and the Concord area would be nice. Boston has it's own board, so check there too!

            Now CT also has a beautiful coastline, Mystic has a lot to see and Old Saybrook is very nice with a great inn on the water: The Saybrook Point Inn. In CT for food DO NOT miss New Haven for pizza and the famous Louis' Lunch burgers. Hot buttered lobster rolls are also a must, but again, check the Southern NE board for details.

            Oh, and don't forget about Little Rhody! Rhode Island has a great seacoast and the city of Providence is a great little city with tons of great food. You'll probably find a great place to stay there, and it's often cheaper than Boston.

          2. Oh my! So many suggestions!! My friend originally proposed this trip as a "chowder tour" but didn't have much of an idea as to what we should to besides sampling chowder. :)

            We'll be going in mid to late October, I actually thought that the leaf season would be over, glad we may be able to catch some of it! We're planning to book our lodging in the next week.

            I don't think we're so much looking to shop in outlet-type shops but we'd certainly be into cool little shops that are around. We're definitely looking to spend some time in Boston and the Providence/Newport area. We weren't really sure of what areas were good in NH and CT. I had forgotten about Salem, but I definitely think that's something we'd love to check out!!

            We have a pretty broad spectrum of interests. Big fans of historical stuff, but also are pretty into kooky, random places as well.

            I'm so, so grateful for all of the help!! I know I didn't really give you much to go on, but I've already gotten so much from these couple of posts!! Feel free to give me more if you think of anything!

            Thanks again!!

            3 Replies
            1. re: raeberak37

              OK - that helps.

              Chowder:

              My personal favorite restaurant chowder is the seafood chowder at Petey's Summertime Seafood on Rt1a, on the beach in Rye, NH. Sit at the bar, the bartenders name is Todd, he's a hoot. Rye is just south of Portsmouth, NH.

              Another good chowder is at the Maine Diner in Wells. It's on Rt1 @ the Kennebunk end of Wells. Again seafood chowder.

              In Boston, the chowder at Union Oyster House would be my suggestion. Union Oyster is one of the oldest restaurants in the country. It also happens to be in the heart of colonial Boston. The buildings in the immediate area date back to before the revolutionary war. Most of the buildings have plaques etc...discussing their history. Just across the Greenway from this area is Boston's north end. This is were Paul Reveres house is & the Old North Church (check out freedomtrail.org) it's also the Italian section of Boston. I LOVE the restaurants in this area. There are two seafood restaurants of note - Neptune Oyster and the Daily Catch. Neptune would have a good chowder, but I'd have a dinner there. Daily Catch is this tiny little place that serves your meal in pan it was cooked in. There are many many great restaurants in this small area, you almost can't go wrong. The length of the line waiting to get in is usually a good indication about the food. I'd just suggest that Modern Pastry is the place for a cannoli.

              Legal Seafood is a local chain that I do not recommend, but they do serve a good clam chowder with these warm crusty dinner rolls.

              If you go to Newport, for your splurge I'd recommend the White Horse Tavern. Oldest continually operated tavern in the US. http://whitehorsetavern.us/

              Other foods to try.

              Lobster Roll. Good one is at the Clam Shack on the bridge in Kennebunkport or Allison's in Kennebunkport. But these are sold seemingly everywhere. A good one should be served on a toasted roll with little to no filler (lettuce or mayo).

              Ice Cream. New Englanders eat more ice cream per capita than any other part of the country. Late October will limit what Mom and Pop ice cream stands are still open. My favorite is Lago's Lone Oak on Rt1 in Rye, NH.

              Full bellied fried clams. The best are on Cape Ann in Massachusetts. Specifically at the Clam Box or Woodmans or Farnhams or Essex Seafood.

              Read eating the coast of New England @ http://www.hollyeats.com/

              Have fun!

              -----
              Petey's Summertime Seafood
              1323 Ocean Blvd, Rye, NH 03870

              Maine Diner
              2265 Post Rd, Wells, ME 04090

              Clam Shack
              2 Western Ave, Kennebunk, ME 04043

              1. re: humin

                Hmm...we had been thinking about eliminating NH from a time perspective, but all of the NH suggestions sound great!! May have to rethink that!

                I have a Legal Seafood near me, so we would probably avoid that for this trip. I just glanced at the menu for the White Horse Tavern, it looks amazing!!

                No one seems to be super excited about lobster rolls but, personally, I can't wait!! Thanks for no filler tip, probably wouldn't have known that. I don't think convincing anyone to get ice cream will be too difficult!!

                Thank you!

                1. re: humin

                  I second Petey's for chowder, Lone Oak's for ice cream, and The Clam Box in Ipswich for fried clams! A nice splurge in Portland for me would be Fore Street. I would call ahead or get there around 5:30. We also LOVE breakfast (not cheap, but very good) at The Stolen Menu in York, Maine.

                  -----
                  Fore Street
                  288 Fore Street, Portland, ME 04101

                  Stolen Menu Cafe
                  127 Long Sands Rd Ste 7, York, ME 03909

              2. I also recommend Petey's in Rye for chowder. You can also hit the Beach Plum in Rye for a lobster roll and ice cream.

                A really cute spot southwest of Manchester is Pickity Place in Mason. The illustration for Little Red Riding Hood were based on the house. It's a fixed menu with 2 choices and the one for October look awesome! http://www.pickityplace.com/

                I would spend some time in Boston, it's a great city.

                3 Replies
                1. re: rizzo0904

                  Pickety Place is a great suggestion.

                  In Boston I would time my trip for a culinary tour of Chinatown. We have also done the one for Boston's North End. Both are great. The Chinatown tour is only on certain days and limited to 10 people and ends with a dim sum meal. You won't have time to shop but you can go back later to interesting places. Everyone on the Chinatown tour had already been on the North End tour. Both are Michelle Topo's tours (but there are several different guides).

                  I would see what Rhode Island ice cream places had the best coffee cabinets. Cant remember the name of the place we went that was supposedly 'the best'.

                  Abbots in/near Mystic CT might not be the best for lobster rolls but I thought it was in a real pretty spot.

                  1. re: dfrostnh

                    dfrost - thanks for the reminder of those michelle topo's tours. gotta do that one of these days.

                  2. re: rizzo0904

                    Oh, NH is definitely back on the trip! Pickity Place looks absolutely wonderful! Thanks so much!!