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New England Fall Loop — a 4-Day Plan You Can Actually Drive
The 4-day version for October: every day fits real transit, opening hours and daylight. Prefer more or fewer days? 4-day plan · 5-day plan · 6-day plan · best time to go.
4
days
786 km
distance
11.2 h
driving
22
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 → White Mountains
🌡 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
12:02
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
12:52
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
14:22
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
Smuttynose Brewerycraft beer & pubslocal & traditional
Taste regionally acclaimed craft beers on tour.
50 min · Portsmouth
09:50
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
10:40
The Music Hallmuseums & heritage
Feel the atmosphere of live performances in a historic theater.
90 min · Portsmouth
12:10
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
13:00
Market Square Daylocal & traditional
Stroll through lively streets filled with food, shops, and local music.
90 min · Portsmouth
open: June
14:30
Portsmouth Blues Festhistory & sagas
Groove to live blues music from talented local and visiting artists.
90 min · Portsmouth
open: August
16:00
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 Stowe
🌡 -6.5–24.7°C · 🌧 ~17 rain days · ☀ 10.7h light
11:09
Vermont Ski and Snowboard Museummuseums & heritage
Discover the history of winter sports through rotating exhibits.
50 min · Stowe · Free will donation $3, families $5
open: Daily except Tu noon-5PM
11:59
Trapp Family Lodge
Take in breathtaking views and echoes of musical legacy.
50 min · Stowe
12:49
Stowe Mountain Resorthiking
90 min · Stowe
14:19
Amtrak
Hear the distant rumble of trains passing through scenic America.
50 min · Stowe
15:09
McCarthy'slocal & traditional
Relish popular local breakfast and lunch dishes in a warm atmosphere.
60 min · Stowe
18:30
Alchemist Pub & Brewerycraft beer & pubslocal & traditional
Admire the rich aroma of exceptional single malt Scotch and unique beers.
75 min · Stowe
Overnight: Stowe
e.g. Ten Acres Lodge Bed & Breakfast · Golden Eagle Resort
Day 4 Woodstock → back to start
🌡 -7.5–25.3°C · 🌧 ~17 rain days · ☀ 10.8h light
10:55
Rockefeller National Historical Parkmuseums & heritagelocal & traditionalhiking
Explore grand mansion halls and hike scenic year-round trails.
50 min · Woodstock · $8, seniors $4, kids 15 and under are fr
open: 10AM-5PM daily
11:45
Billings Farm and Museummuseums & heritagelocal & traditionalhistory & sagas
Discover Vermont’s rural heritage on a lively, working farm.
50 min · Woodstock
12:35
Feast and Field Marketlocal & traditional
Enjoy live music and fresh, local farm-to-table meals.
90 min · Woodstock · Free, Special Events $20
open: Food: 4:30-7:30 Music: 5:30-8 Campfire Music: 8-9:30