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May 15, 2008 09:04 AM

Memorial Day Road Trip- First Time to Maine (HELP!)

My BF and are I planning to head up to Maine from NYC for the memorial day weekend...neither of us have ever been and were at a loss of where to go and more importantly where to eat!
A quick mapquest search puts Portland 5 + hrs away, and Kittery 4.5 hrs...
Since we only have Friday - Monday we dont have a whole lot of time to explore.
Any suggestions would be greatly appreciated,


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  1. In terms of restaurants and other things to do, if it were me I would stay in Portland. It's a great jumping off point to explore some of the coast and it's got the greatest cluster of top-notch restaurants. Whenever I have friends or family visiting from out of town for the first time, I always take them to the Two Lights Lobster Shack in nearby Cape Elizabeth: They serve whole lobster, lobster rolls, fried clams, etc. Their chowder is also very good. Plus, the view cannot be beaten.

    I'd also try to get a reservation at Fore Street. Hugo's, 555, Fish & Co., and Cinque Terre are a few others to look into if Fore Street doesn't work out. I'm sure others will have additional suggestions. There are so many great places to eat in Portland.

    1. Staying in Portland is a great idea but let me lure you north to the Bath, Brunswick area. I would not take a trip to maine without trying the Robinhood Meetinghouse in Georgetown, just over the bridge from Bath. M Gagne is doing a commercially available cream cheese biscuit that is out of this world, better at the resto. I would also suggest Back St Bistro in Brunswick. Take a drive up the coast and do a sunset sandwich on the deck at Sebasco Lodge on 209, an old style maine resort, great fried clams there as well. I am a long time, part time resident of Vacation land and there are too many places to go and eat than would fit into a weekend. If you wander north, drive to the end of 209 for a walk on the best beach in NE, Popham and enjoy the sunset at Sebasco afterwards, make a late dinner reservation for the Meetinghouse and you will have spent a glorious day in Maine.

      1. I would recommend driving a stretch of Route 1 which goes right along the coast from New Hampshire all the way to Canada. The most picturesque areas are north of Portland — Falmouth, Freeport (home to LL Bean), Booth Bay, New Castle, Pemaquid Point, and Camden are the places to spend the night. I'd pick where you are going to stay then find the good eats. If your heart is set on Portland then JenBoes later suggestions are perfect (my favorite is 555). It's hard to go wrong if you head to the coast.

        1 Reply
        1. I am prejudiced as I live there in the summer, but Ogunquit is a beautiful town worth at least a drive through, a walk on the beach and marginal way (a 1+ mile path along the rocky coastline) and one good meal. There is Barnicle Billy's where you can get excellent clam chowder, steamers, and lobsters and sit out on the deck and drink the best rum punch this side of Jamaica. Or have lunch or dinner at MC Perkins Cove, beautiful views and good food. Then, drive up to Kennebunkport or Portland to continue the good eats. It is worth driving north to the Bath area- I have never been to Robinhood but would love to try. But in that same area near Georgetown is the Five Islands Lobster Company- a beautiful place to sit on the water looking out to the five pine covered islands, eating crab claws, lobsters, steamers, fish sandwiches, etc. (do not use the bathrooms there, though). Wherever you go , have a great trip.

          6 Replies
          1. re: emilief

            thanks for the tips...after doing more online seraching seems like we should head to portland, and make a day trip to freeport / cape elizabeth..

            1. re: lemonyc

              Maine is my favorite destination and I've stayed in many places. Be sure to at least drive through Ogunquit and up the coast to Portland. There are wonderful views and great places to eat along the way. Have a wonderful time and enjoy it all.

              1. re: othervoice

                May I add my two cents, I agree with the other people who have given you the advice about Ogunquit, Its a great place to stay and to eat. Most places are now open. There is a great downtown area though not to large, but a nice place to stroll and have ice cream or a coffee and walk to the town beach, at night. I'm not to sure how much of a central area there is in Portland to walk and shop and just hang out,so I cant comment on it. but it is a large city. There is a really nice place to stay in Ogunquit at this time of the year. There rates haven't gone up to the normal summer season rates as yet. ( And you can drive along the coast up to wells and then to Kennebunkport and up route 1 along the coast to Portland, Hope this helps, Earle Ct.

                1. re: Earle

                  Since the original poster is coming from NYC, I doubt she'll consider Portland, at around 75,000 people, a large city. That said, it is the largest in Maine. There are many places to stroll, shop and eat in Portland's Old Port area, which is also within walking distance from the downtown. It's a great place to visit and get a feel for Maine, if you don't have time to get down East, particularly if you wind your way up the coast on Route 1 a bit.

              2. re: lemonyc

                If you really want to get away go to Rockland Maine and take the ferry over to Vinalhaven. You will find absolutely NOTHING to do, which is why we go there and are going on Memorial Day weekend. We don't like crowds, only fresh air and real Mainers. Before heading on the ferry eat at the Rockland Cafe, it is on Main St. and they have fried clams with belly..No frills though, no frills on Vinalhaven. Just pure Maine fresh air and 'do nothing' time. We love it.

                1. re: nhgator

                  Is the restaurant still open on Vinalhaven?? Too cold but the quarries are a great hike.

            2. Given the timeframe, Portland or the southern coast makes the most sense to me. However, in my opinion, the coast is an overdeveloped tourist trap! ( and I live here).
              For a different( and more authentic) view of Maine, continue up to Bethel( 1.5 hrs north of Portland). Spend a night in Bethel....head to Rangely( 1 hr from Bethel) spend a night at the Rangely Inn.
              You can't go wrong with Portland......or anywhere else in Maine for that matter. I just find the coast to be too busy in the summer. The further "downeast " you go, the worse it gets. Western Maine is beautiful and realtively uncrowded in the summer.