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Long weekend on Maine Cost - feedback on plan?

Maine hounds -

My wife and I are escaping the swamp of DC for a long labor day weekend in Maine. As she's pescatarian, Maine is food heaven for her. I've looked at many threads here and some other places and have pulled together the idea of a plan for our meals there but would love any additional advice or feedback any of you have. The biggest gaps in my plan are for a place for dinner in Blue Hill/Deer Isle on Saturday, and a place to stop for lunch driving back to Logan on Monday. We have a preference for local/simple places, but the budget is flexible.

General logistics: We're flying into Boston on Thursday evening, driving up to Portland, and staying at the West End Inn for two nights. We're then driving up the coast on Saturday to a place we're renting in Brooksville for two nights before driving back down to Logan on Monday.

When staying in Brooksville we're looking to spend time in Acadia as well. I know it will be a lot of driving on the way back (esp on a Monday of a holiday weekend), but the fare difference (logan vs. portland) was too much to pass up, and gives us more leeway in the dining budget.

Detailed plan:

Thursday:
late dinner at Local 188 - reasonably close to West End Inn, varied menu depending on how hungry we are. (estimate we won't get to Portland until 8-9 pm).

Friday:
Breakfast at West End Inn
Lunch at Bite into Maine truck by the lighthouse
walk around Portland, afternoon drink and oysters at Eventide
Dinner at Bar Lola

Saturday:
Breakfast at West End Inn
hit the road, head up the coast
Lunch at Five Islands Lobster Co. in Georgetown
Ideas for place for dinner in Blue Hill or Deer Isle?

Sunday:
Ideas for Breakfast/place to get picnic supplies in Blue Hill?
Head to Acadia, hike and picnic for lunch
Dinner at Thurston's

Monday:
Drive back down to Boston - Ideas for good (different) places to hit on the way back? Our flight doesn't leave Boston until the evening, so a great lunch stop on the way back to break up the drive would be most appreciated.

Many thanks!

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  1. nice list!
    Local 188 is a perfectly fine choice, but I would say the food has been a bit uneven lately--for West End options, I'd say Outliers (my new favorite--), Pai Men Miyake, Caiola, or LFK (which is more of a bar with very good food) would be better choices.

    2 Replies
    1. re: sultanaboudreau

      Thanks S - do you know how late Outliers' kitchen is open on a weekday? I looked around the web, but could only find that the bar is open until 11 pm but no info about the kitchen. Website photos looked beautiful, though!

      1. re: babbuino

        It's my new favorite in town!
        At least until 10:45 PM, I believe? opentable.com takes reservations for Outliers for as late as 10:45--Tuesday-Saturday.

    2. Red's Easts in Wicasset is generally cited as having one of the best lobster rolls around (I agree) if your planning on taking Rt1S instead of 95 on Monday, line gets long though. Nearby Sea Basket has been reported to have great fried items but I haven't tried

      I've also had solid seaside meals at Harraseekett Lunch, which is near the flagship LLBean in Freeport

      3 Replies
      1. re: sbs401

        Totally disagree about Reds. It is very mediocre, not even close to the best lobster roll in Maine. I can't figure out why there is always such a long line, except that people like their grease. Sea Basket IS much better. We have had way better lobster rolls than Reds in lots of places, most recently at Graffam's in Rockport. Love Bagaduce Lunch in Brooksville.

        1. re: sbs401

          Seabasket is excellent for fried fish, whole belly clams, oysters (in season, of course.)

          Red's Lobster roll is just shelled lobster in a roll; you have to decide if it's worth the wait. Line moves very slowly.

          I once had the best inexpensive lobster roll I've ever had at a little drive-up in the middle of Blue Hill....sorry, can't remember the name!

        2. I can give a first-hand report that Five Islands is well worth the visit.

          Second hand, I have heard only good things about the "Bite Me" truck and Eventide.

          If you're going to be walking around the Old Port area, stop in at Blue Rooster on Dana Street and try the fried Brussels sprouts.

          1. The only thing I might add to all the already excellent suggestions in the Portland area is on your first night. If you get into town on the late side (9 ish) and then check in, clean up, etc, you might be pushing the service limits time-wise on some food choices. That would lead me to direct you more towards Pai Men Miyake or Boda which both have a real good later night crowd and, like Local 188, just a few blocks from the Inn.
            Friday is good. If you plan to do the blind tasting menu at Bar Lola I'd advise calling and letting them know beforehand. I think like the opportunity to prepare and you'll get a better product.
            Another option besides Red's (which is great if you can deal with the line - about 25 people when I rode past today... in the rain!), AND you plan on hitting LL Bean in Freeport, then possibly Jameson Tavern right near the store. Taken over by the former Fisherman's Grill owner in Portland, great fried clams.
            Enjoy!

            1 Reply
            1. re: bobbert

              thanks for the advice - I think you might be right about our arrival time on the first night. I'll definitely call Bar Lola ahead of time - the "feed me" option looked great.

            2. We enjoyed Cleonice in Ellsworth during our last visit to the Blue Hill area. It was also a September visit, and the local produce was at it's prime. Others who get there more often can better comment on how the kitchen has been recently.

              On your way back Monday, it really depends on whether you plan to do the slow Route 1 drive, or the faster Rte 95.

              Plenty of options in Portland, of course. Or closer to your destination the Portsmouth area. I was going to suggest a late lunch/early dinner at Black Birch, but they are closed on Monday. Maye something in-town Portsmouth--the last couple of times we've been to the Portsmouth Brewery for lunch I've been impressed, nice casual lunch time fare using good quality ingredients.