Day 1 — Wheels Up at Dawn, Lobster Rolls by Lunch

New England Road Trip 2026 · Day 1 · Tuesday, June 2 · Portland, Maine

Every good family trip seems to start the same way — except this one started a little earlier than most. My alarm went off at 3:11 a.m. so we could make the drive to the airport. That's less "pretending to be a morning person" and more "are we even people yet." But this trip had been on the whiteboard for months — a big New England loop with the four of us — so we loaded a minivan full of snacks and four bleary travelers and pointed it at the airport. Destination: Maine.

Getting there (barely)

We flew Richmond → LaGuardia → Portland, and I'll be honest: the LGA connection came down to the wire. We hit the jet bridge at last call, the kind of sprint-through-the-terminal moment you laugh about later and absolutely do not enjoy in the moment.

Worth it, though, for the views out the window. On the descent into LaGuardia, the kids had their faces glued to the glass over the Manhattan skyline and the Statue of Liberty — not a bad consolation prize for a 3 a.m. wake-up.

Then came the part I'd been waiting for — the islands and that rocky, folded coastline of Maine sliding under the wing on the way into Portland. We grabbed the minivan at the Jetport and were rolling by late morning.

First stop: Portland Head Light

We didn't even bother with the hotel first. Went straight to Fort Williams Park and the Bite Into Maine food truck parked right there with the lighthouse behind it — about as Maine as a first lunch gets. Two lobster rolls: the wasabi and the Connecticut (warm butter). Eaten at a picnic table under the flag, blue sky, lighthouse over our shoulders.

Quick confession that'll be a running theme this trip: our 10-year-old does not do seafood — or, honestly, most foods. The truck kiosk runs a short menu, so while the rest of us went to town on lobster, he made do with a bag of chips and didn't complain once. I'm calling that a parenting win. We poked around the lighthouse, the big lawns, and the tide pools afterward — first real "we're on vacation" exhale of the trip.

Into the Old Port

Checked in at the Hilton Garden Inn down on Commercial Street — room wasn't ready, which is exactly the excuse you want to go wander Portland's Old Port on foot. First detour: The Holy Donut, where they make donuts out of Maine potatoes. The chocolate beat the maple, for the record.

Then a bit of travel-day magic: walking the waterfront, we stumbled onto the Maine Narrow Gauge Railroad right as the 2:00 train was boarding, so we just… hopped on. A short, breezy ride along Casco Bay behind a little antique narrow-gauge engine. Completely unplanned, and exactly the kind of thing the kids end up remembering most.

Dinner, Old Port edition

For dinner we did Eventide Oyster Co., which is the move with kids — lively, casual, no white tablecloths, but seriously good oysters and drinks. We ran a little Maine oyster flight: Bombazine, Wet Smack, and Pleasant Cove, with mignonette. After much deliberation I can report I'm a bold-and-briny guy — Bombazine took the crown, Wet Smack a close second, with the milder Pleasant Cove bringing up the rear.

From there I snuck down the alley to Novare Res Bier Café — a beer lover's hideout with a list that goes on for days. I kept it crisp with a Tipopils, the cult Italian pilsner, on the waitress's rec.

We capped the night at Rí Rá by the harbor. Our picky guy finally got his chicken tenders — and then promptly got so deep into a Narnia book that he forgot to eat them. I went the other direction entirely: a massive Bacon Blu burger and a Maine Beer Co "Lunch" IPA. No notes. So full.

Calling it

That pre-dawn start eventually caught up with us, so we made a game-time call and bumped the Portland Sea Dogs game — turned out you can catch a Thursday late-morning game on the way out of town, which is a better fit anyway (more on that in a couple days).

A small tinkerer's footnote, since it's part of the story: I've been building a little homegrown AI travel sidekick that quietly logs our stops as we go — the colorful play-by-play behind these posts. More on that another time.

Day 1: lighthouse, lobster, potato donuts, a surprise train, and a kid who'd trade it all for chicken tenders. Tomorrow, we chase a beach down in Kennebunkport.

Up next → Day 2: Kennebunkport beach day (and a Sea Dogs morning).