For the love of Portland, ME

January 10, 2024

In Maine, Kennebunkport was our first love. It became a yearly tradition to head to Boston for a night, then drive to Kennebunkport for 2-3 nights. The quaint, small town sucks you in with its charm and the local pubs and shacks with the best lobster rolls and clams casino keep you craving more.

One trip with friends a few years ago found us driving to Portland for the day for a little more variety, and we found an extremely walkable, beautiful, small city with tons of great restaurants to explore. Then Delta announced a non-stop flight and, without a second thought, we dumped Kennebunkport. Cold, I know, and we will reconcile one day. For now, it’s Portland.

Our first trip was best described as an eating frenzy, with walking in between. Although we would have had to walk to Boston and back to make a dent in our eating and drinking. The second and third time, we abandoned the forced march approach and settled in.

In between the excessive eating and drinking, we did manage to circumnavigate the entire city on every visit. We walked the entire west end, including the neighborhoods, we walked around the entire east end along the water, then headed up Munjoy Hill. We loved seeing the neighborhoods filled with young families and corner markets and bakeries — there seems to be a bakery every hundred feet. And there is actually history (the city was founded in 1632) and interest (Eastern Cemetery, a working port, etc.) here, in addition to all the breweries, distilleries, and restaurants.

Enough with the pleasantries, let’s talk food and drink.


Tandem Coffee & Bakery

For a great pastry, coffee, sweets, breads:
For all-out gluttony:


Fore Street

For finer dining:
  • Twelve – multi-course prix fixe, which we usually don’t love, but this is not to be missed.  Sit at the chef’s counter if you can.
  • Fore Street – the original restaurant that put Portland on the map.
  • Scales – on the harbor, same ownership of Fore Street.  Bar sitting is best, with a cool ice collar on the bar.


The Chef’s Counter at Twelve


For lobster rolls (and other stuff):
  • Eventide Oyster Co. – for oysters, lobster rolls, and everything on the menu.  There’s a constant line here for a reason.  Put your name on the list and head next door to The Honey Paw from the same owners for drinks and an app. The Honey Paw is also worth its own stop, for a different spin than the rest of the seafood heavy restaurants in Portland (and don’t miss the fry bread).
  • The Highroller Lobster Co. – I was skeptical at first of Highroller (too many overly positive reviews), but our last trip found us there twice for the fish and chips and outstanding lobster roll.  Enough said.
  • Portland Lobster Company – or PLC as the locals call it.



The Highroller Lobster Co.

For cocktails:
Others worth mentioning:
  • The Shop – a wholesale oyster place, but you can enjoy a dozen of the freshest oyster there with a cold beer.
  • Cong Tu Bot – for clever Vietnamese.
  • Terlingua – for inventive and delicious barbecue.
  • Duckfat – which, after all these years, still has a line for their fries.

Blyth & Burrows

The Independent Ice Co.

Central Provisions


There are a bunch. We barely made a dent with visits to Hardshore (primarily known for its very floral gin) and Maine Craft Distilling, which is much more polished and established, with some of its signature drinks sold bottled and canned. For beer, the city is a beer drinker’s dream, but Allagash is the local favorite.

If you haven’t been to Maine, make it a summer or fall destination. Unlike us, if longer US vacations are your thing, combine a few days in Kenne with a few days in Portland (only about a 45-minute drive) to see what we love about both. Tell Kennebunkport we said hi, and we’ll be back. And don’t miss the lobster rolls.

Want to Engage Shea for your upcoming project?

Get In Touch