The Coast Road to Boothbay — Baseball, Beer, and a Legendary Lobster Shack

New England Road Trip 2026 · Portland → Boothbay Harbor, Maine · Thursday, June 4

Travel days on a road trip are their own kind of fun: you check out of one place, point the van at the next, and let the stops in between write the day. Ours took us out of Portland and up the coast to Boothbay Harbor — by way of a ballgame, a brewery, the L.L.Bean flagship, and the most famous lobster shack in Maine.

A short morning at Hadlock Field

We'd bumped it from earlier in the trip, so we started the day at the 11:00 Portland Sea Dogs game at Hadlock Field — the Double-A Red Sox affiliate, right in town.

Full honesty: this one didn't go the way I pictured it. We'd wandered straight into a giant end-of-school-year field-trip day — think thousands of kids and a parking lot full of buses — on a boiling-hot morning. The ballpark itself is a fine, no-frills minor-league yard, but between the heat and the crowds (and a souvenir ball-cap mission that fizzled when we couldn't flag anyone down), Owen and I tapped out after the second inning and pointed the van north. Some days the move is knowing when to cut your losses and get on the road — and we had a long, lobster-filled drive ahead.

Lunch at Maine Beer Co, Freeport

Twenty minutes up I-295 we pulled into Maine Beer Co in Freeport for a late lunch — and this one was a hit for everybody. Wood-fired pizza for the kids (an Owen-approved win), and for me, the tap board: eight of their own beers on draft, including the two you come for, "Lunch" and "Dinner." I ran a flight to taste my way across it, light to heavy.

It's a genuinely family-friendly brewery — windows into the brewhouse, cocktails and wine and sodas for everyone who isn't chasing IPAs, and just down the road from where we were headed next.

L.L.Bean, for the binoculars

No trip up US-1 is complete without a stop at the L.L.Bean flagship in Freeport — the one with the giant boot out front, open more or less around the clock. We were on a mission: a pair of binoculars for the next day's whale-and-puffin cruise. (We grabbed a couple of other odds and ends too; that store has a way of finding things for you.)

Red's Eats, Wiscasset

Then came the one I'd been waiting for. If you've ever driven US-1 through Wiscasset and hit a wall of traffic, congratulations — you've found the Red's Eats line. It's a tiny red shack on the corner with a lobster roll that's pure bucket-list Maine: something close to a full pound of lobster meat piled on a butter-griddled split-top bun, butter on the side.

We ordered two of them for Kristen and me, with chicken fingers for Owen and a burger for Brooklyn, and ate out on the little picnic deck over the Sheepscot River. It's a splurge — market price, and it shows — but this is the lobster roll you make the drive for.

Into Boothbay Harbor

From Wiscasset it was another half hour up US-1 and down ME-27 to Boothbay Harbor, where we checked into the Fisherman's Wharf Inn right on the water. After a long travel day we kept the evening low-key — we settled in at the inn's waterfront restaurant, the kids split a soft pretzel and got a little screen time, and we just sat back and soaked up the harbor view as the light went gold.