
Base: a room on or near Dock Square for both nights. Today starts in Boston: the Downeaster leaves North Station at 8:50 a.m. on weekdays and reaches Wells at 10:36 a.m., and a taxi from the Wells Transportation Center to Dock Square takes about 17 minutes. After that the day is on foot: Dock Square, the Mathew Lanigan Bridge and Lower Village on the Kennebunk side of the river are all within a few minutes’ walk, and they are free to wander. Pace: easy: a morning on the train, a long lunch, a slow afternoon in the village.
Breakfast at the Boston Public Market
Where to eat: start at the Boston Public Market, 100 Hanover Street, a year-round indoor market of New England food vendors a short walk from North Station. It opens at 8 a.m. from Wednesday to Saturday; vendor hours vary, so pick a counter with coffee and something warm and take it with you.
Walk to North Station with time to spare and find the Downeaster on the departures board. The train runs north through the Merrimack Valley and into New Hampshire before it reaches the Maine coast.
The Downeaster to Wells
The Amtrak Downeaster is the train between Boston and the Maine coast. On weekdays the 8:50 a.m. from North Station reaches Wells at 10:36 a.m.; on Saturdays and Sundays the same departure arrives at 10:38 a.m. Wells is the closest stop to the Kennebunks.
The Downeaster Café, in every train, sells snacks, light meals and hot and cold drinks, so a second coffee on the way north is easy.
Expert tip: arrange your taxi or rideshare from the Wells Transportation Center before you leave Boston. Cars can be scarce on a December Friday, and the station building is open from 5:30 a.m. to 9 p.m. if you need to wait inside.
Lunch in Dock Square
Where to eat: drop your bags at the inn, then walk to Alisson’s Restaurant at 11 Dock Square, a local landmark for 50 years. Lunch runs every day from 11 a.m. to 4 p.m. It takes walk-ins only, no reservations, so an early lunch on arrival day avoids the wait.
Kennebunkport Inn, at One Dock Square, was built as a tea merchant’s home and sits on the rise above the square, which makes it an easy first base.
Dock Square, the river and the lights
Spend the afternoon on foot. Dock Square is a small triangle of shops and galleries at the head of the harbor; cross the Mathew Lanigan Bridge to Lower Village on the Kennebunk side and look down the river toward the sea. Shops along both banks are hung with wreaths and garlands in December.
On Christmas Prelude’s opening Friday, December 4, 2026, the Dock Square tree lighting starts at 5:30 p.m. with carolers from the Kennebunk High School Chamber Choir, and the tree is lit at 6 p.m. The Cape Porpoise lobster-trap tree is lit at 7 p.m. the same night. On other weekends, the square stays lit through the season.
Where to eat and stop
- Breakfast · Boston Public Market — 100 Hanover Street, Boston; open 8 a.m. Wed–Sat; vendor hours vary.
- Lunch · Alisson’s Restaurant — 11 Dock Square; lunch 11 a.m.–4 p.m. daily; walk-ins only.
- Dinner · Batson River Brewing & Distilling (Kennebunk) — 12 Western Avenue, Lower Village, across the bridge from Dock Square.
- Quick stop (snack): Downeaster Café — the café in every Downeaster train: snacks, light meals and hot drinks.
- Quick stop (other): Christmas Prelude in Dock Square — the town’s December festival; the opening tree lighting is in Dock Square.
Boston Public Market → North Station: about 10 minutes on foot. North Station → Wells by the Downeaster: about 1 hour 46 minutes. Wells Transportation Center → Dock Square by taxi: about 17 minutes (8 miles). Dock Square → Lower Village over the bridge: about 5 minutes on foot.
Where to stay
- Kennebunkport Inn (Dock Square) — a historic inn at One Dock Square, built as a tea merchant’s home, steps from the square.
- Nonantum Resort (Ocean Avenue) — or a resort hotel at 95 Ocean Avenue on the river, a short walk from the square; check winter dates when you reserve.
Dinner: at Batson River Brewing & Distilling, 12 Western Avenue in Lower Village, across the bridge from Dock Square.
Tomorrow: the shore road east along Ocean Avenue to the fishing harbor at Cape Porpoise.
Bad-weather plan
Rain or a hard freeze on Day 1? The train and Alisson’s are indoors, and Lower Village’s cafés and Batson River are a short walk across the bridge, so keep the walk short and the lunch long.
Stay: Dock Square base · Anchor: Dock Square · arrange the Wells taxi ahead
Good to know: The sun sets a little after 4 p.m. in early December, so arrive by lunch to see the river in daylight. Christmas Prelude runs December 3–13, 2026; the full 2026 schedule is on the Christmas Prelude app.





















