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New England Fall Loop: the Day-by-Day Itinerary
This loop is New England at its most photogenic. White church steeples rise over villages ablaze with maples, covered bridges cross slow rivers, and roadside stands sell cider donuts still warm from the fryer. Time it to the foliage front and the whole drive glows.
New England Fall Loop is a 640 km loop (self-drive). It works best as 4–6 days; the plan below is the 5-day version for October, built from 178 verified places, with real road-routed transit times, opening hours and daylight checked.
Customize this plan → 4-day plan · 5-day plan · 6-day plan · best time to go
5
days
786 km
distance
11.2 h
driving
26
curated stops
💡 Good to know for this plan
- Foliage sweeps north-to-south from late September — book inns months ahead and check state foliage trackers to time the Kancamagus.
Day 1 Boston → Portsmouth
🌡 0.9–24.6°C · 🌧 ~19 rain days · ☀ 10.8h light
09:00
National Park Servicehikinghistory & sagas
Learn about Boston's historic sites and download the Freedom Trail app.
50 min · Boston
09:50
Urban AdvenTourshiking
See a variety of bike rentals, including e-bikes, with helmets provided.
50 min · Boston · $40-100/day
10:40
Sampan Newspaperhistory & sagas
Uncover rich Chinatown history in this paper.
50 min · Boston
12:52
The Strawbery Banke Museummuseums & heritagehikinghistory & sagas
Step back in time through preserved historic houses.
50 min · Portsmouth
open: May-late Oct 10AM-5PM, late Oct-Dec on some weekends 10AM-2PM and for
13:42
Peirce Island Poolcraft beer & pubsswimming & baths
Swim and relax in one of New England's largest public pools.
90 min · Portsmouth · $2 ($1 for Portsmouth residents)
open: Open from mid June to late August
15:12
Smuttynose Brewerycraft beer & pubslocal & traditional
Taste regionally acclaimed craft beers on tour.
50 min · Portsmouth
16:02
Portsmouth Gas Light - Downtown Brick Oven Pizzacraft beer & pubs
Enjoy delicious pizza from a brick oven in a vibrant complex.
60 min · Portsmouth
18:30
Portsmouth Brewerycraft beer & pubsmuseums & heritage
Enjoy award-winning brews and hearty pub fare in a lively downtown setting.
75 min · Portsmouth
Overnight: Portsmouth
e.g. Sheraton Harborside Hotel · Hilton Garden Inn
Day 2 Around Portsmouth
🌡 0.9–24.6°C · 🌧 ~19 rain days · ☀ 10.8h light
09:00
John Paul Jones Househistory & sagas
Visit the preserved home of a naval legend.
50 min · Portsmouth · $6 adults, $5 seniors/veterans/AAA membe
open: Memorial Day-Columbus Day: 11AM-5PM daily
09:50
The Music Hallmuseums & heritage
Feel the atmosphere of live performances in a historic theater.
90 min · Portsmouth
11:20
Amtrak Downeastermuseums & heritage
Hear the whistle of the train arriving at the station.
50 min · Portsmouth · $6-25
open: M-F 5:45AM-1:45AM, Sa-Su 6AM-1:45AM
12:10
Market Square Daylocal & traditional
Stroll through lively streets filled with food, shops, and local music.
90 min · Portsmouth
open: June
13:40
Portsmouth Blues Festhistory & sagas
Groove to live blues music from talented local and visiting artists.
90 min · Portsmouth
open: August
15:10
Halloweenlocal & traditional
Join parades and spooky fun for all ages in the historic town.
90 min · Portsmouth
open: October
16:40
Flatbreadcraft beer & pubs
Relish organic, wood-fired pizzas in a cozy, open-space setting.
60 min · Portsmouth
Overnight: Portsmouth
e.g. Sheraton Harborside Hotel · Hilton Garden Inn
Day 3 White Mountains
🌡 -7.3–24.6°C · 🌧 ~18 rain days · ☀ 10.7h light
11:36
Wildcat Mountainhiking
90 min · White Mountains
13:06
Santa's Village
90 min · White Mountains
See the remaining 2 days of the 5-day plan →
Route map
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