Like a small-town Brooklyn, in Maine
Portland: 48-Hour Escape from Boston
Maine's foodie port city, with the most restaurants per capita in the US, 90 minutes north of Boston.
Portland: Maine's foodie port city, with the most restaurants per capita in the US, 90 minutes north of Boston.
At a glance
Portland, Massachusetts is a 1 hr 30 min drive from Boston, best visited May-October. Like a small-town Brooklyn, in Maine. Top things to do: Portland Head Light, Old Port wandering, Eastern Promenade. Where to eat: Eventide Oyster Co., Duckfat, Fore Street. Stay at The Press Hotel or Portland Harbor Hotel.
61
of 100
Escape score
Best paired with a second town
A good day and a half, with an evening to spare.
- Drive
- 1 hr 30 min from Boston
- Best window
- May-October
- Typical stay
- ~$227/night
Escape score: what there is to do and eat (40%), typical weekend lodging cost (30%), drive time (25%), rounding (5%). Computed from our own guide data, never from paid placement.
Why here
Portland, Maine is a city of 68,000 on a peninsula in Casco Bay, 90 minutes north of Boston. It has the most restaurants per capita of any US city, and the Old Port district is a working fishing wharf turned food destination, with lobster shacks, oyster bars, and a brewery on almost every block. The Eastern Promenade is a mile of waterfront park, and you can take the Amtrak Downeaster here from North Station in 2.5 hours, no car needed. It's the Northeast's best small-city food trip.
Portland was a shipping and fishing port before it was a food town, and it never stopped being either. The working piers on Commercial Street still unload lobster and groundfish, and the food scene grew out of the waterfront, not separate from it. The turn came in the 2000s, when chefs like Sam Hayward of Fore Street and the team behind Eventide put Portland on the national map, and the breweries, with Allagash, Shipyard, and Bissell Brothers within a mile, followed. The result is a city where you can eat a brown butter lobster roll, drink a world-class sour, and watch a lobster boat come in, all in a five-block walk.
A weekend in Portland is a walk-and-eat weekend. Wander the Old Port cobblestones, eat at Eventide and Duckfat, walk the Eastern Promenade at sunset, and drive 15 minutes to the Portland Head Light at Fort Williams, the oldest lighthouse in Maine. Take the Amtrak Downeaster so you can drink. Two nights lets you add a ferry trip to Peaks Island in the bay.
The plan
48 hours in Portland
Same town, two different weekends. Pick the arrival that matches your Friday.
Friday, on arrival
Check inThe Press Hotel
From ~$250/night
Boutique hotel in the Portland Press Herald building, 110 rooms, each themed like a 1920s newsroom. Walking distance to the Old Port. The design hotel...
Leave Boston after work: the 1 hr 30 min drive lands you here in the evening.
Friday night
Dinner, then the main streetEventide Oyster Co.
The oyster bar that put Portland on the food map. The oyster platter and the brown butter lobster roll are the orders. No reservations, expect a wait.
Eat first and walk it off after. Most small-town kitchens stop seating by 9.
Saturday morning
First stopPortland Head Light
Free. The oldest (1791) and most photographed lighthouse in Maine, in Fort Williams Park, 15 minutes from downtown. The cliff walk is 30 minutes. Park...
Saturday midday
LunchDuckfat
Belgian fries and sandwiches. The poutine and the milkshake are the moves. Counter service, 8 seats, takeout the move.
Saturday afternoon
Second stopOld Port wandering
Free. Cobblestone streets, 19th-century brick warehouses now full of restaurants, bars, and shops. Commercial Street faces the working waterfront. All...
Saturday night
DinnerFore Street
Wood-fired everything in a 19th-century warehouse. The mussels, the roasted carrot, and whatever is on the hearth are the orders. Reserve 2 weeks ahea...
Sunday morning
Last stop, then homeEastern Promenade
Free. A mile-long waterfront park with views of Casco Bay and the islands. The paved path connects to the Old Port. Best at sunset.
1 hr 30 min back to Boston still leaves you the afternoon.
Timings are a suggestion, not a schedule. Shift the whole plan by how late you leave.
The Basecamp
Where to stay in Portland
The Press Hotel
Boutique hotel in the Portland Press Herald building, 110 rooms, each themed like a 1920s newsroom. Walking distance to the Old Port. The design hotel in town.
Portland Harbor Hotel
In the heart of the Old Port. 96 rooms, a courtyard, and walking distance to every restaurant. The most central stay.
The Westin Portland Harborview
A 1927 Art Deco tower downtown, fully restored, with a spa and a rooftop bar. The high-rise, walk-to-everything stay.
What to do
Portland Head Light
Free. The oldest (1791) and most photographed lighthouse in Maine, in Fort Williams Park, 15 minutes from downtown. The cliff walk is 30 minutes. Parking is tight summer weekends.
Learn more ↗
Old Port wandering
Free. Cobblestone streets, 19th-century brick warehouses now full of restaurants, bars, and shops. Commercial Street faces the working waterfront. Allow 2 hours.
Learn more ↗Eastern Promenade
Free. A mile-long waterfront park with views of Casco Bay and the islands. The paved path connects to the Old Port. Best at sunset.
Learn more ↗Pack for Portland
Beach & coast kit
Curated for sand, surf, and slow tide-pool afternoons in Portland.
Portable beach umbrella
Real shade that survives a Gulf breeze.
See price on Amazon →Low-sand beach chairs
The four-leg kind that do not slowly sink out from under you.
See price on Amazon →Waterproof dry bag
Keeps phones and keys dry from the car to the sand and back.
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Mineral-based, reef-friendly, and reef-town appropriate.
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Where to eat
Eventide Oyster Co.
The oyster bar that put Portland on the food map. The oyster platter and the brown butter lobster roll are the orders. No reservations, expect a wait.
Duckfat
Belgian fries and sandwiches. The poutine and the milkshake are the moves. Counter service, 8 seats, takeout the move.
Fore Street
Wood-fired everything in a 19th-century warehouse. The mussels, the roasted carrot, and whatever is on the hearth are the orders. Reserve 2 weeks ahead.
Most reviewed on Yelp
The most-reviewed restaurants in Portland. A solid indicator of where locals actually eat.
Street & Co.
Seafood
Hot Suppa
Breakfast & Brunch
The Porthole Restaurant & Pub
Diners, Seafood, Breakfast & Brunch
Review counts and ratings are curated from Yelp and may change over time.
Go even deeper
Side trips near Portland
Once you've settled into Portland, these nearby towns are close enough to fold into the same weekend without moving your basecamp.
20 min from Portland
Freeport
20 minutes north, the home of the L.L. Bean flagship store open 24/7, an outlet-mall walkable downtown, and the Wolfe's Neck farm trails.
15 min from Portland
Cape Elizabeth
15 minutes south, the headland with Portland Head Light, the oldest lighthouse in Maine, and Fort Williams park with clifftop trails.
On the calendar
Coming up in Portland
Events happening in town, refreshed weekly.
Refreshed weekly
Nov 7 to 8
First Tracks: Northeast Snow Show
Portland · Thompson's Point
This winter-season festival brings together ski passes, outdoor gear exhibits, local food and drink, and family activities. Visitors can make an energizing waterfront weekend out of gearing up for the upcoming winter sports season.
Getting there
Drive logistics
From Boston, take I-95 North to I-295 North. ~110 miles, about 1.5 hours. Or Amtrak Downeaster from North Station, 2.5 hours, ~$30. The train drops you at Thompson's Point, 10 minutes from the Old Port. Summer Friday traffic on I-95 is brutal, leave by 2pm.
Drive time
1 hr 30 min
Best time
May-October
Questions & Answers
Portland weekend FAQ
Portland is about 110 miles north of Boston, roughly 90 minutes by car via I-95 North, or 2.5 hours on the Amtrak Downeaster from North Station.
Yes. The Amtrak Downeaster runs from Boston's North Station to Portland in about 2.5 hours, ~$30 one-way. It continues to Freeport and Brunswick.
Portland, Maine consistently ranks at or near the top of US cities for restaurants per capita, driven by its working fishing port and the farm-to-table movement.
Yes. At 2 hours by Amtrak Downeaster or car, Portland is the best food-and-coast weekend from Boston, with a working fishing pier, the Old Port warehouse district, and a top small-city restaurant scene.
Yes. The Amtrak Downeaster runs from Boston's North Station to Portland in about 2 hours, with a station walkable to the Old Port downtown, so a car is not needed.
The Dispatch
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