Psst... We're working on the next generation of Chowhound! View >
HOME > Chowhound > Southern New England >
Aug 4, 2011 02:05 PM

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!!

  1. Click to Upload a photo (10 MB limit)
  1. The original comment has been removed
    1. You're trying to cover three boards. Southern Maine is the Northern New England board; I'd recommend starting in Portland, which is a great food town, with a wide variety of creative restaurants for many tastes and budgets. Boston has its own board, and while Boston is no San Francisco, there are very many options, and you can eat well for weeks without doubling up. South of Boston is the Southern New England board; since I live in RI I'm partial to the Providence dining scene, which also has many creative modern restaurants along with historical favorites (mostly in the Italian-American genre). Depending on your route, there's also New Bedford to consider, even if you don't get out to the Cape.

      Without getting as snarky as CCG, he does have a point. Are you interested in a specific type of dining? Are you after cutting-edge white-tablecloth stuff, do you want shacks on the water, diners, family-style ethnic places? When, exactly, in October? That's important, because a lot of the more al fresco places shut down by or on Columbus Day weekend. Yet if you want to tour northern New England in, say, the first two weeks of October you'll find lodging to be an issue, as out of town "leaf peepers" descend.

      You really need to give more detail. I think you'll find that the more specific the question (and the more it looks as if you've done some reading before posting) the more likely you are to get better quality replies.

      1 Reply
      1. re: Gin n Tonic

        Very well said and far more appropriate than my original, and thankfully deleted, comments.

        rae, do provide some details and I'm sure you will get much help, myself included.

      2. What part of Connecticut are you interested in staying near?

        3 Replies
        1. re: TrishUntrapped

          How funny, Im planning the exact trip in reverse! Id definitely say check out New Haven and maybe the CT wine trail in Litchfield.

            1. re: TrishUntrapped

              We had been thinking about New Haven but that's not set in stone.

            2. Let me apologize for being so vague. I'm so flustered by this trip at the moment. My friend decided she wanted to plan the trip herself, which was fine by me as the whole thing was her idea. I found out last week that she had yet to do anything and I was nervous that we would have difficulty booking hotels if we waited much longer. I'm also super new to this site, so I didn't really realize all the details I would need to include.

              The trip is being touted as a chowder tour, so I suppose that would be my primary focus in terms of dining but I know that I personally can't eat nothing but chowder for 8 days. We will be there in mid to late October. We had been thinking we would try to do 4 areas in that time, leaving us about 2 days in each area. I'm sure we could spend a week in one spot in a lot of New England but, since neither of us have ever been to any part of it, we thought we would try to get a sampling of different areas and possibly plan future trips to further explore.

              We were thinking that we'd start in Portland, ME, then make our way to Boston, RI (Providence? Newport?) and then finish in CT. I have no idea where to go in CT. I had been thinking the New Haven area but, admittedly, that's the one leg of my trip I haven't much researched yet. My husband is uber-paranoid and is convinced that the two of us are going to pick up a serial hitchhiker and be murdered or something, so we would certainly want to stay in areas that are safe, generally speaking.

              We're on a bit of a budget (both teachers!!) so we aren't really looking for a ton of fine dining, but we would certainly consider a splurge or two. In terms of activity besides food (I know this site is dedicated to food, but if there's anything you think may be interesting...) we would certainly be interested in historical type activities but we also love kooky, random things.

              I hope this helps to clarify and, again, I apologize for any confusion!

              2 Replies
              1. re: raeberak37

                in NEWPORT
                - the seafood chowder at Perro Salado
                - the scallop chowder at the Mooring

                there are reasonable B&Bs in newport off season and if you arent big drinkers or want to splurge an extra $10 on a cab you can book in much cheaper Middletown.

                Perro Salado
                19 Charles St, Newport, RI 02840

                1. re: raeberak37

                  I'll leave discussions of Portland to the appropriate board, ditto Boston where it seems you've already recieved some good advice. (Although, in addition to checking out the Freedom Trail (must do!) you can also take an historic harbor cruise out of Charlestown, and a visit to the Kennedy Library is worthwhile if you have interest. If it were me, I'd spend one night in Portalnd and three in Boston. Have lobster in Maine and stop in Essex MA.for fried whole belly clams on your way to Boston. If colonial history is of interest, in addition to the Freedom Trail you can drive 30 minutes west to Lexington/Concord.

                  For your 5th and 6th nights you could choose between Newport RI with its nautical locale and historic mansions, or maybe the Cape if you want a more laid back off season beach locale. Either place will have many threads on great eating options from fancy to ultra casual. Late October, however, will limit some options at either location. For your 7th and 8th night I would pick Mystic Ct. an historic colonial seaport village with some nice dining opps and a short ride to the lovely towns of Stonington, Old Lyme and Old Saybrook among others. I would skip New Haven although the pizza is renown, the city itself is far from my favorite to be kind. In all location think regional seafood. Maine is lobster, Mass (north shore and the Cape) for clams, Rhode Island for 'stuffies', clam cakes, and clear (no cream) chowder, and everywhere for Cod, Haddock, Sole, Flounder, and scallops.... all broiled, fried, baked stuffed, pan seared, or.pan roasted.

                  You'll get the most out of this board if you come back and post once you've picked your locations. People are happy to direct you to their favorite hidden and not-so-hidden gems. All they seek in return is a trip report after you visit to see how you liked their recs.

                  Here are some links that may help in your decision:






                2. Hmmm... Your question was a challenge for me because of Connecticut. A lot of towns and cities close early in Connecticut, but since nightlife doesn't seem to be your focus, I think I can make a few recommendations. I would do Boston, Newport, and Mystic.

                  After leaving Boston you could make a lunch stop in Fall River, Mass which is en route to Newport. In Fall River you can sample some wonderful Portuguese food! I had lunch recently at Sagres restaurant. They serve hefty-sized lunches with a fair amount of seafood options, including Caldeirada A Portuguesa and Mariscada - Portuguese Bouillabaises. They also have some nice meat options, especially the Cornish hen. Here is the link to the main site. Click on the menu tab, scroll down and click on the menu for larger type.

                  Sights: Fall River is known for Lizzie Borden, who was accused, and later acquitted, of the 1892 double axe-murder of her father and stepmother. Fall River is also known for Battleship Cove, the world's largest collection of World War II naval vessels. If you have any interest in WWII it's a gerat visit.

                  Battleship Cove:
                  Lizzie Borden B&B and Museum:

                  Newport, I'll leave to others.

                  Mystic: Where to eat? I enjoyed breakfast at Kitchen Little:
                  I'll leave the chowder rec's up to others.

                  Sights: There is a lot to do in and around Mystic

                  It's also close to the Foxwoods and Mohegan Sun Casinos. The casinos have some interesting dining choices.

                  Where to stay: I stayed at the Steamboat Inn and loved it!

                  Other Mystic lodging options:

                  I didn't choose New Haven or Hartford in CT because I think there is more to do in the Mystic area.

                  Sagres Restaurant
                  177 Columbia St, Fall River, MA 02721

                  Kitchen Little
                  135 Greenmanville Ave, Mystic, CT 06355