We’re back again, Boston.
🍁 In just a few weeks, colorful backroads, country fairs, and pumpkin spice-flavored everything will be waiting up north. And you’re going to be ready.
👀 What’s on tap today:
A town that’s basically Stars Hollow IRL
Leaf peeping that’s worth the roadtrip
Cider donuts, cider donuts, cider donuts!
Up first…
THE ITINERARY
Your perfect fall weekend, mapped
🌳 Fall in New England is basically a sport — and New Hampshire plays it better than anyone else. Between the postcard towns, the jaw-dropping mountain views, and the snacks that all involve cinnamon sugar, you could honestly throw a dart at the map and land somewhere magical. But if you’d like a little structure to your leaf-peeping pilgrimage, here’s our playbook to planning the ultimate autumn getaway.
FRIDAY EVENING
Settle in at Littleton
⛰️ By the time you arrive, you’ll see why Littleton is a go-to starting point for a fall weekend. It’s the right mix of small-town charm and White Mountain access, with plenty of ways to ease into the season. Take a walk down Main Street, browse the local boutique shops, and grab dinner somewhere hearty before settling into an inn for the night. Tomorrow’s a big day.
Things to try:
Dinner at Schilling Beer Co. (ask for a table with riverside views — you’ll thank us later)
Browsing Little Village Toy & Book Shop for your next road trip read
A cozy stay Stay at Thayers Inn or Adair Country Inn & Restaurant
SATURDAY
Maximum foliage
🚞 This is the day you block out for the outdoors — and trust us, it’s worth it. Start with a ride on a scenic vintage train or a drive along the Currier & Ives Scenic Byway, a route dotted with rolling farmland, historic villages, and foliage that gives the much-buzzed-about ( much more crowded) Kancamagus Highway a run for its money. Break up the drive with stops at covered bridges, country stores, or roadside stands. Then, spend the afternoon at a local fall festival, where pumpkin contests, hayrides, and live music might have you thinking “Should I move here?” by the end.
Things to try:
Take a foliage zipline or chairlift ride for a unique bird’s-eye view of the fall colors
Check out the Warner Fall Foliage Festival or Berlin RiverFire Festival (pumpkins, crafts, and good vibes guaranteed)
Explore charming artisan shops or roadside craft stands for quirky local treasures
SUNDAY
Lean into the fall clichés (they’re clichés for a reason)
🍎 You didn’t come all this way to not eat a cider donut, so today is about the greatest hits: orchards, corn mazes, hayrides, pumpkins, and apples you swear you’ll bake into a pie (but probably won’t). It’s classic, it’s fun, and it’s the perfect way to wrap up a weekend of peak fall energy.
Things to try:
Getting lost in the corn maze at Collins Farm (bonus points if you don’t cheat)
Fresh cider donuts (best eaten warm, sugar on your fingers)
Apple picking at Windy Ridge Orchard (and yes, hard cider counts as “supporting local agriculture”)
🌟 Feel like swapping apples for pumpkins, or scenic drives for hiking trails? Find more ways to plan your perfect New Hampshire fall trip here.
QUICK QUESTION
🗳️ You’re visiting New Hampshire in October. What’s one thing you have to do?
ONE LAST THING
🍁 Did you know peak foliage in New Hampshire doesn’t hit all at once? Up north, the leaves start turning in late September, while the southern parts usually wait until mid-October.
That means if you chase the color from top to bottom, you can ride the peak-foliage wave for weeks.
— Written by Tori Waltz, Studio/B, Boston Globe Media’s branded content studio (The editorial team was not involved in the creation of this B-Side Extra Edition)
🍂 Thanks for reading! We’re on our way to see how many cider donuts is too many (for research).
💜 Special shoutout to today’s sponsor, Visit NH, for sponsoring this extra B-Side send and reminding us why fall is New England’s best season.