Massachusetts
Small-Town Weekend Getaways from Boston
Maine lobster ports, Gilded Age Newport, and White Mountains villages, all reachable by train or a short drive.
At a glance
Boston has 3 small-town weekend escapes, each with a full 48-hour guide to where to stay, what to do, and where to eat. Drives run from 1 hr 30 min to Newport and 2 hr 30 min to North Conway. The headline draws: The Breakers, Portland Head Light, Mount Washington Cog Railway. Most of these towns are at their best May-September.
- Escapes
- 3 towns
- Drive range
- 1 hour 20 minutes to 2 hours 30 minutes
- Closest
- Newport, 1 hr 30 min
- Best months
- May-September
Pick your trip
Three ways to start planning a weekend from Boston.
Shortest drive
Newport
Newport is 1 hr 30 min from Boston. Gilded Age mansions, a cliff walk, and the America's Cup harbor, 90 minutes south of Boston.
Most to do
Portland
3 mapped stops in Portland, at 1 hr 30 min out. Like a small-town Brooklyn, in Maine
Worth the drive
North Conway
North Conway is the longest haul at 2 hr 30 min. A White Mountains village with outlet shopping, the Cog Railway, and the best fall color in New England, 2.5 hours from Boston.
The short version
Small towns near Boston worth a 48-hour trip
Boston weekend trips head north into Maine, south to Rhode Island coast, and into the White Mountains. Within two to three hours you reach a lobster-and-brick Maine port, a Gilded Age Rhode Island seaside town, and a New Hampshire mountain outlet village. These are weekend trips from Boston built on coast, lobster, and mountain air.
Portland (2 hours north, Maine) is the food-and-brick port city with a working fishing pier, the Old Port warehouse district, and one of the best small-city restaurant scenes in the country. Newport (1.5 hours south) is the Rhode Island Gilded Age seaside town with ocean-drive mansions and a cliff walk. North Conway (2.5 hours north) is the White Mountain village, with outlet shopping, the Conway Scenic Railroad, and trailheads into the Whites.
Compare the Boston escapes
Drive time, character, best season, and the one thing to do first, for every town within reach of Boston.
| Town | Drive | Character | Best time | Do first |
|---|---|---|---|---|
| Newport | 1 hr 30 min | Like the Hamptons, with mansions | May-September | The Breakers |
| Portland | 1 hr 30 min | Like a small-town Brooklyn, in Maine | May-October | Portland Head Light |
| North Conway | 2 hr 30 min | Like Stowe, with outlets | June-October (fall color) or January-March (ski) | Mount Washington Cog Railway |
On the calendar
Coming up in the Boston escapes
Events happening in the small towns themselves, not the city.
Refreshed weekly
Nov 6 to 11
Bring A Friend
North Conway · Settlers Green
This signature multi-day shopping and entertainment celebration features daily in-store events, giveaways, and special activities across the outdoor village. It makes a lively autumn weekend trip for visitors looking to kick off their holiday shopping in the White Mountains.
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.
Nov 12
A Newport Songbook with Historic Music of Newport
Newport · The Newport Mansions
This evening concert celebrates Newport's rich musical heritage with 19th-century performances and songs tied to historic local salons and theaters. It offers cultural travelers a distinctive historic experience within coastal Rhode Island.
The roundup
3 Best Weekend Escapes Near Boston | 48-Hour Trip Ideas
Three easy micro-escapes from Boston for food, coast, and mountain air, all close enough to make a real weekend feel longer.
Read the guide →All Boston escapes
3 weekend trip ideas from Boston, sorted by how far you have to drive. Vibes covered: food, beach, history, mountains, nature.
1 to 2 hours
2 escapes from Boston
2+ hours
1 escape from Boston
What to do
The top attraction in each Boston escape town, pulled straight from the 48-hour guides.
Portland
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.
Newport
The Breakers
$30. The 70-room Vanderbilt summer 'cottage,' 1895, the grandest of the Newport mansions. Audio tour, 75 minutes. The great hall is 50 feet high. Reserve ahead summer weekends.
North Conway
Mount Washington Cog Railway
$75. A 1879 steam cog railway up Mount Washington, the second-steepest in the world. 3 hours round trip to the 6,288 ft summit. The summit is 30 degrees colder, bring a jacket. Reserve 1+ month ahead.
Questions & Answers
Boston weekend FAQ
Newport (1.5 hours), Portland (2 hours), and North Conway (2.5 hours) are the strongest small-town escapes from Boston, covering a Rhode Island Gilded Age seaside town, a Maine food port, and a White Mountain village.
Yes. The Amtrak Downeaster runs from Boston's North Station to Portland, Maine in about 2 hours, with a station walkable to the Old Port downtown.
Newport is about 1.5 hours south of Boston, known for Gilded Age mansions on Ocean Drive, the Cliff Walk, and a walkable wharf downtown.
Newport (1.5 hours, Gilded Age mansions), Portland, Maine (2 hours, the Old Port food scene), and North Conway (2.5 hours, White Mountain trails) are the best weekend getaways from Boston, covering Rhode Island coast, Maine lobster, and New Hampshire mountains.
Newport: May-September; Portland: May-October; North Conway: June-October (fall color) or January-March (ski).
The escapes split by mood: beach (Newport, Portland); history (Newport); food (Portland); mountains (North Conway); nature (North Conway). Every one is a 48-hour trip with specific places to stay, visit, and eat.
Newport, about 1 hr 30 min away. Like the Hamptons, with mansions Start with The Breakers.