4 Days in Portland, Maine: Lobster + local brews

Portland Head Lighthouse at Fort Williams Park

There’s a quality of life in Maine which is this singular and unique. It’s absolutely a world onto itself.

Jamie Wyeth

A trip full of beer, lobster, and epic New England views? Sign me up! When Steve and I were deciding on an anniversary trip in October, Maine seemed like the perfect four-day getaway. Southwest flights were cheap – and quick! – and the leaves were out in full force. It was a little cold at the end of October, but still gorgeous.

Lobster roll in Maine
Lobster roll from Alison’s in Kennebunkport

We stayed in an Airbnb in Munjoy Hill, the neighborhood just outside of downtown Portland. It’s an easy walk or short drive to downtown, and there’s a lot happening in the neighborhood. (I definitely recommend an Airbnb – just not the one that we stayed in. It was FRIGID the whole time and the homeowners didn’t seem interested in turning up the heat.)

I also recommend renting a car because there’s so much to see outside of Portland. We wanted to spend a day in Kennebunkport, and, if we’d had more time, we would’ve gone to Bar Harbor.


  • Eventide Oyster Co (Downtown): Seafood w/an Asian spin. This was Steve’s first lobster roll and he thought the steamed bao bun was a little too buttery, but this is should definitely be on your to-try list.
  • Blue Spoon (Munjoy Hill): Insanely good Brussels sprouts w/bacon at a cute bistro on the hill
  • Holy Donut (Downtown): HOLY is right. In Maine, they make donuts from potatoes, and they are AMAZING. They’re so dense, I could barely make it through one – but I managed.
  • Forage Market (Munjoy Hill): Delicious breakfast sandwiches and a small flower market 
  • Otto (Munjoy Hill): Great pizzas with a few locations in Portland. (Heads up that the cocktails weren’t great, though.)
  • Highroller (Downtown): Our favorite lobster rolls! So many varieties, which I loved because I don’t eat mayo. (Also, ick, What a way to ruin lobster.) Plus, they have massive homemade whoopie pies. (Maine claims to be home of the whoopie pie, but I was raised in Pennsylvania. That’s not true.)
  • Blythe & Burrows (Downtown): Speakeasy w/really great cocktails. Our bartender was excellent and gave really good recommendations.
  • Central Provisions (Downtown): The place everyone recommended. Small plates, really great bone marrow. We had to wait a bit for a table, but it wasn’t too bad.
  • LB Kitchen (Munjoy Hill): Obsessed with the sweet and salty oats I had here and haven’t been able to recreate them.


  • BREWERIES! You can’t go to Portland and skip the breweries. There are SO many.
    • Rising Tide (Munjoy Hill): A favorite! We went 2x and loved the fresh-shucked oysters on site.
    • Foundation, Battery, Austin Street, Allagash (Industrial Way): This industrial grounds has several breweries all within walking distance, plus a great distillery.
    • Bissel Brothers (just outside of downtown): Cool industrial area with a winery and the International Cryptozoology Museum
    • Oxbow Brewery (Munjoy Hill): Smaller pours, wine and ciders, and the Duckfat Friteshack outside. (Yes, get the frites. They’re worth it.)
  • Portland Head Lighthouse (15 min south of Portland): Portland has no shortage of lighthouses; this is its most famous. Located at Fort Williams Park, it’s a quick trip outside of the city and also home to the Bite into Maine, a lobster food truck that was highly recommended. (We were too full to try it!)
  • Portland Flea for All (Downtown): Really cool market with so many vintage things to check out
  • Kennebunkport (40 min south of Portland)
    • Ignore the fastest route on GPS and drive down Ocean Ave to pass the Bush family compound and stop to take pictures of the gorgeous views
    • Lots of cute shops, including Daytrip Society
    • Stop at Alison’s for lobster rolls – and any other seafood
    • If it’s earlier in the season, check out the Clam Shack! It was closed when we were there.

My parents have always wanted to go to Maine, so I think we’ll definitely be back in the coming years. I’d prefer to go in earlier October or late September and have a little more time to spend outside of Portland. There’s so much more of Maine to see.

If you’ve been to Portland and the surrounding area, drop your recommendations in the comments!

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