One Week in New Hampshire for Fall Foliage Lovers: A Detailed Trip Itinerary
An autumnal itinerary for slow travel lovers who want to get a bit off-the-beaten-path
Detailed Trip Itineraries
Welcome to my August 2025 Detailed Trip Itinerary post! These itineraries are packed with secret tips I’ve found, must-see spots, and recommendations to help you make the most of your travels. For this post, I’m taking you to a place that’s known for its jaw-dropping seasonal foliage, easy hikes, small-town charm: New Hampshire.
The first two days are available to all subscribers, but the rest of this itinerary will be exclusively for paid subscribers. If you love what you see, stay tuned! More detailed trip itineraries for destinations around the world will be available soon. Now, let’s dive in….
One Week in New Hampshire for Fall Foliage Lovers: A Detailed Trip Itinerary
Day 01
Fly into New Hampshire by way of Portland International Jetport or the Boston Logan International Airport and start your trip off with a drive to Jackson, an idyllic New Hampshire town known for its historic charm, cozy accommodations, and iconic covered bridge!
Check in to your stay at The Wentworth for an old-timey, yet totally modern accommodation in town or the nearby Inn at Whitney’s Farm for a more rural fall feel. This charming village gives you immediate access to both the White Mountains and the eastern start of the Kancamagus Highway, without feeling overly touristy.
Take a walk through town to stretch your legs after the drive. Start at the covered bridge, then wander past the white-steepled church and into the cozy J-Town Deli for a warm drink or pastry.
Secret Tip: The best golden hour light hits the town green and the bridge from 4–5:30PM in late September. I’d make sure to bring a light jacket! It can cool down quickly, even on sunny days.
Next, head back to The Wentworth for an easy, yet elevated dinner at the hotel’s onsite Alpine Tavern. Sample the restaurant’s cozy offerings before getting a good night’s rest (tomorrow is a big drive day!).
Day 02
Grab breakfast to-go across the street from The Wentworth at Autumn Nomad Café (the baked goods here look amazing!), then hit the road: this moring is for the Kancamagus Highway.
Secret Tip: “The Kanc”, or the Kancamagus Highway, is one of the area’s most popular routes to experience the fall foliage, so the parking lots at the viewpoints fill up quickly! For the best way and time to visit, drive the Kancamagus Highway east to west first thing in the morning, even as early as sunrise if you can manage it. That may mean you’ll need to hit breakfast a bit later in the day, but you’ll be rewarded with fewer crowds, less traffic, and softer lighting through the golden-hued trees.
This drive has been on my bucket list for YEARS and is roughly 35 miles, but you'll want to give yourself most of the morning to mid-afternoon to take in the stops:
Sugar Hill Overlook (not to be confused with the town!)
Pack a picnic lunch ahead of time or stop for a late lunch in Lincoln at White Mountain Bagel Co. to refuel.
Then, hit up the vibrant red Flume Covered Bridge and Flume Gorge before checking-in to your new hotel for the evening. For something rustic-luxe, try the Launchpoint Lodge which offers an independent mountain escape with smart tech-enabled technology throughout the resort. If you prefer something quieter, look at Lumen Nature Retreat in Woodstock. No, it’s not related to the mysterious company in Severance, but it is known for it’s glamping and premium cabin options.
Once you’ve settled in, opt for dinner at The Common Man in Lincoln just down the road. Dine amid candlelight, a stone fireplace, and a menu built for fall (think Nantucket pie, New England pot roast, and lots of wine!).
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