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There are plenty of reasons to take a trip through New England at any time of year. The rolling hills and rocky coastlines are green and lush in the summer. In the winter, you can take advantage of the blanket of snow that covers the place from December through March, or just cozy up by the fireplace.
But at its core, New England is a fall place. As someone who grew up in New Hampshire, as soon as the air gets just the slightest bit of chill, I get nostalgic for home and start immediately planning an escape northeast, up the coast of Maine.
Not only do you get sunny, crisp days and fiery red and orange tree tops, but you get to shop for the items New England does best — cozy flannels, corduroy barn jackets, wool sweaters in rust, greens, and reds — while you’re at it.
While this itinerary is written as a road trip from New York to Portland, Maine, you can think of it as a take-what-you-want shopping guide through Providence, Boston, Portsmouth, Kittery, the Kennebunks, and Portland. There’s plenty to pick and choose from here, no matter where you start or how you get there.
Day One, AM: Providence
New York isn’t that bad in the fall. It’s actually pretty nice. But drive 30 minutes in any direction and suddenly you realize what you’ve been missing: autumn in actual nature. If you’ve already restocked your closet for cold weather in the city, now you get to take those pieces out to an ideal backdrop and feel the crunch of fallen leaves underneath those new fall boots.
Stop in New Haven for some pizza if you’re passing through around lunch time (Sally’s and Pepe’s are where it’s at), but save all your shopping energy for Providence. Three hours up the coast from New York, this college town is small enough to see in a day, but has a bunch of shops worth checking out. See our map of where to shop in Providence for nine shops to hit, or get the short list below.
Head to ten-vendor vintage collective The Vault for furry coats, colorful maxi dresses, cute leather jackets, bright dresses, and reasonably-priced flannels (which will quickly become the theme of this trip).
Talulah Cooper is a cute jewelry shop that stocks everything from punky, snake-shaped cuffs to delicate ID necklaces and bracelets.
And finally, Clover is a great stop for clothes with an avant-garde vibe that are still highly wearable (New England is nothing if not practical). The store carries men’s and women’s pieces from brands like Oak, YMC, Humanoid, and Earnest Sewn.
Day One, PM: Boston
Boston is just an hour’s drive north of Providence, so you can head up in the afternoon, check into a hotel, and still have plenty of time to shop before you enjoy the town’s stellar restaurant scene. If you want to be stationed in a prime shopping zone, look for a hotel or AirBnB near Newbury Street or Boston Common.
While Faneuil Hall and the North End have lots of charm, Newbury Street is where the locals go to actually shop. This stretch of street right near Boston Common is where all the designer flagships are located (the multi-story Chanel store and a well-stocked Rag & Bone shop are both worth a look). But the spots not to miss are some of Boston’s best independent stores — hit up concept stores All Too Human (on nearby Clarendon) and Alan Bilzerian on Newbury for the best browsing.
If you’ve got time, check out vintage menswear and curiosity shop Bobby from Boston as well as hidden streetwear shop Bodega, two completely different types of men’s shops that are equally fun to visit. The first feels like walking onto a movie set; the second is accessed through a hidden door in an actual working bodega.
Day Two, AM: Cambridge
After breakfast, hit up anything you missed before heading to Cambridge, which will feel like a small town compared to the brick streets of Boston. Don’t miss lingerie shop Forty Winks; Oona’s Vintage & Modern, one of Boston’s best curated vintage stores (that recently reopened under new ownership); and The Garment District, a huge warehouse of vintage organized by decade, with a pay-by-the-pound room (well, more like pile) downstairs and a costume shop-within-the-shop called Boston Costume.
If you like cooking — or even just eating — stop at Formaggio Kitchen’s original Cambridge location on your way out. This local cheese shop stocks some of world’s best (and most hard-to-find) spices and ingredients, plus you can pick up a few snacks for the road.
Day Two, PM: Portsmouth, New Hampshire, and Kittery, Maine
Most people don’t even realize New Hampshire has beaches, but the small coastal stretch of the Granite State between Massachusetts and Maine is gorgeous and super laid-back.
Portsmouth, a naval town, has the most going on. It’s just an hour’s drive from Boston and is right on the border of Maine, so you can easily make a day of exploring Portsmouth and neighboring Kittery, Maine, a small town just on the other side of the Piscataqua River.
While there’s no shortage of shops in Portsmouth, there are only a few where you might actually want to buy something. (And hey, keep in mind that New Hampshire has no sales tax! Major plus.)
Stop by Bliss, a charming women’s boutique that’s the perfect place to shop for cozy sweaters, coats, and everyday jeans. The store has great options for extras, too, from boots to bags to Hanky Panky undies.
Nearby Old As Adam is only open on the weekends, but it’s a must-stop for anyone into vintage menswear. For men more into modern options, check out Sault, which stocks preppy-ish basics and accessories.
Downtown Kittery, just over the bridge into Maine, is teeny tiny (just a few blocks), but it’s packed with cute spots. Folk, an adorable women’s, kid’s, and gift shop, is worth the detour alone. Next door you’ll find Vinyl Vault and Lil’s Café, a vintage record store and cute coffee shop that are run by the same owners.
Grab a coffee and pastry at Lil’s before you head across the street to Tayla Mac, another cute gift shop filled with sweet stationary, handmade ceramics, jewelry, kid’s stuff, and some apparel (though the clothes here are less tempting than at Folk).
Kittery also boasts a pretty stacked outlet scene, which is definitely worth hitting up (you could save it for the morning on your way out if your day is feeling too packed). The huge Kittery Outlets complex off Route 1 features discount shops from Gap, J.Crew, Barbour, Lululemon, Levi's, Aldo, Express, and many more.
If you're in the mood for something a little more local, Kittery Trading Post is the spot. This huge sports and outdoor emporium is quintessential Maine: You can shop everything from flannels to winter boots, coats, sleds, canoes, skis, and much more.
Day Three: Route 1, Ogunquit, and the Kennebunks
As soon as you hit the road in Maine, you’re going to start seeing signs for antique stores about every 100 feet. You’re going to want to stop off at a few... especially if you’re coming from New York (if just to prove to yourself that cheap antique stores exist).
Maximize your antiquing opportunities by taking a slightly more scenic drive up Route 1 instead of Interstate 95. Shops literally line the highway, so you can pull off whenever you see one that tickles your fancy. I happen to like the warehouse-style spots like Hidden Treasures right on the outskirts of Kittery toward York, where several vendors sell their wares in one place. But really, you can’t go wrong.
When you get to Ogunquit, pull off to stretch your legs. This coastal town is known for its gorgeous, cliff-y beaches and art galleries. You can take a short (and easy, paved) "hike" over by the cliffs, but if you just hang out in the small downtown area, be warned: The shops here are generally terrible (think things your mom would want to buy on a beach vacation).
There is one saving grace, though, and that’s Blacksmith’s Antique Mall. This huge, multi-vendor shop is jammed with all kinds of cool treasures to discover, from vintage clothes to baseball cards to jadeite pottery.
Continue up Route 1 to Kennebunk and Kennebunkport, a quaint town you may have heard of because the Bush family vacations here. The downtown area can feel like a bit of a tourist trap, too, but there are a few good spots to shop.
Daytrip Society (and its sister shop for kids, Daytrip Junior) features Maine vacation-friendly goods with a glossy sheen, from beach bags made out of vintage sails to Peg & Awl canvas goods and pretty guide books to Acadia National Park.
Just over the foot bridge, The Green Tangerine is a good bet for dresses and casual T-shirts and sweaters (though its sister shop, The Pink Tangerine, is for Lilly Pulitzer fans only). Downstairs in the same complex, you’ll find another cool antique shop, Contents Preserved, which just opened up earlier this year. The shop has more of a curated feel than the flea market vibes of the antique malls.
If you want to chill out a bit instead of driving the final hour up to Portland, Kennebunkport has a bunch of cute B&Bs and a great collection of (actually pretty swanky) hotels called the Kennebunkport Resort Collection, which includes several award-winning properties.
Days Four and Five: Portland
Well, you’ve finally arrived! While still not huge, Portland is big enough that you can spend a few days walking around the Old Port and cute downtown — and even more if you use the town as a jumping off point for day trips up the Maine coast or inland.
There’s a lot of good shopping to explore here, so you should definitely consult our full map of where to shop in Portland. If you want to limit it to the heavy-hitters, definitely check out Judith, a chic women’s shop on Market Street right by the water, and nearby Portland Dry Goods, which has wonderful preppy-leaning basics for men and women including amazing sweaters, coats, sweatshirts, and boots.
After you’ve gotten the fancy version of a general store (at Dry Goods as well as Portland Trading Company), make sure you spend some time in an actual Maine general store. Renys sells everything from canned goods to outdoor gear, and is definitely the best spot in town to pick up a discounted flannel, wind jacket, or some wool socks.
More & Co is the best shop for gifts, and features a bunch of made-in-Maine brands (in a way that’s anything but cheesy). The ceramics here are especially nice.
For vintage and antiques, check out the Portland Flea-for-All, a huge, multi-vendor indoor flea market with great mid-century furniture, wool coats and sweaters, retro decor, and records.
But there's so much more to explore — see our map of where to shop in Portland for even more recommendations from a Portland local.