Falling for Kittery: A Fall Guide to Kittery, Maine
There's a smell that hits you the second you step out of the car in Kittery come fall - salt air, woodsmoke, and something faintly cinnamon-sugar that you will absolutely need to investigate. From September through early November, this little corner of Maine turns into its best version of itself: crisp mornings, a river that glows gold at sunset, and just enough sweater weather to make you feel smug about packing one. The summer crowds have gone home. The leaves along the coast are showing off. And the whole seacoast, from Kittery Point down to Portsmouth and York, is basically begging to be explored at a slower pace, ideally with a donut in hand. Here's how we'd spend it.
Walk Through Three Centuries of History (No Textbook Required)
Kittery is the oldest town in Maine, and it does not let you forget it - in the best way. Start at Fort McClary State Historic Site in Kittery Point, where a black-and-white 1844 hexagonal blockhouse stands guard over the mouth of the Piscataqua River like it's still on duty. Climb up for the view, poke around the old powder magazine and earthworks, and claim a picnic spot. It's open daily through Columbus Day, so there's no excuse not to swing by. A few minutes down the road, Fort Foster trades ramparts for rocky shoreline, a fishing pier, and walking trails that turn genuinely spectacular once the foliage kicks in.
Want the full story behind all this old stone and salt spray? The Kittery Historical & Naval Museum packs three centuries of shipbuilding, naval history, and Gilded Age glamour into one small, mighty building. It keeps a limited fall schedule, so check hours before you go.
Sip Your Way Through the Local Beer Scene
Kittery's brewery game has quietly become a real reason to visit. Tributary Brewing Companyand Woodland Farms Brewery are both just minutes from downtown, which means you can knock out a flight and a little outlet shopping in the same afternoon - efficient, if not exactly balanced. And Woodland Farms deserves a special shoutout: it was Maine's first non-alcoholic brewery, and its lineup of craft NA beers (IPAs, sours, even a stout) is good enough that "I'm not drinking tonight" stops being a taproom deal-breaker. For something with a bit more mischief, Loaded Question Brewing and Odd By Nature Brewing are worth the short drive - the latter is almost as famous for its cocktail program as its beer. Grab an outdoor table, let the fall air do its thing, and call it a perfect Saturday.
Where to See Fall Foliage Near Kittery, Maine
Kittery sits right on Maine's Fall Foliage Coastal Route, and honestly, some of the best color around here isn't buried in the woods, it's hanging right over the water. Cruise Route 103 through Kittery Point toward York and watch the sea and sugar maples put on a show against the ocean. Peak color usually lands somewhere in late September to mid-October, though Mother Nature doesn't exactly RSVP, so keep your plans loose. Bike or drive down to Seapoint Beach or the Nubble Lighthouse in nearby York for the kind of fall light that makes your camera roll look like a postcard rack.
Fall Festival Season on the Seacoast
If there's a better excuse to wander around outside eating something off a stick, we haven't found it. Here's what's on the calendar within easy reach of the inn:
Laudholm Nature Crafts Festival in Wells (September 12–13, 2026) is one of the most respected juried craft shows in New England, with 140-plus exhibitors on the gorgeous grounds of the Wells Reserve at Laudholm, which was stunning even before anyone brought handmade pottery into it.
Apple Harvest Day in downtown Dover, NH (October 3, 2026) is the Seacoast's biggest fall street party, with 60,000 people, endless vendors, live music, and, as the name promises, apples in every form you can imagine.
York's Harvestfest & Kidsfest (October 17, 2026) takes over Short Sands Beach with craft vendors, live music, and enough family activity to tire out even the most determined toddler.
Ghosts on the Banke at Strawbery Banke Museum in Portsmouth (October 16–17 and 23–24, 2026) is Halloween done the historic way, with trick-or-treating house to historic house among 300 years of jack-o'-lantern-lit homes. Spooky, but the friendly kind.
The Portsmouth Halloween Parade (October 31 at 7 pm) is the seacoast's wildest night out, a totally grassroots, come-as-you-are march from Peirce Island through downtown Portsmouth, with hundreds of costumed marchers and thousands more cheering from the sidewalk. No sign-up, no rules, just show up in your best getup and go.
Farmers' markets and craft fairs pop up around the seacoast most fall weekends, so it's always worth a quick check for what's happening the week you're in town.
Farm Stands, Cider Donuts, and the Best Kind of Sugar High
Let's be honest: no fall trip to Maine actually counts unless it involves a warm cider donut eaten slightly too fast in a parking lot. Spiller Farm in Wells has been growing apples, pumpkins, and berries since 1894, and its farm store turns out fresh cider and donuts that make the drive worth it on their own. Bonus: weekends from mid-September through mid-October bring free wagon-ride farm tours out into the orchard - low effort, high charm. Head a little further south to Hampton Falls, NH, and you'll hit Applecrest Farm Orchards, the oldest continuously operating apple orchard in the country, which throws a Fall Harvest Festival every weekend through October complete with bluegrass music, horse-drawn hayrides, a petting zoo, and cider donuts fresh enough to burn your fingers.
Either stop makes a perfect detour on a foliage drive. Bring a growler of cider back to the room. We won't judge.
Shopping and Dining Around Town
Kittery punches well above its weight for a town this size, and fall is the season to actually enjoy it instead of just passing through. The Kittery Outlets stretch for more than a mile along Route 1 and cover everything from J.Crew to Coach, with Kittery Trading Post anchoring the whole thing as a destination in its own right. For something less mall, more Maine, head to Kittery Foreside, a walkable little cluster of restaurants, studios, and shops near the Naval Shipyard entrance, perfect for a coffee, a gallery wander, and dinner. Out toward Kittery Point, Chauncey Creek Lobster Pier serves lobster-in-the-rough right on the water through Columbus Day - BYOB, no fuss, just a picnic table and a very good view. Cap it off with lobster rolls and chowder at Warren’s Seafoodacross the street from our inn, and you've got a full day of eating and browsing without ever leaving town.
Make Water Street Inn Your Fall Home Base
Stay within walking distance of Kittery Foreside and minutes from Portsmouth, the outlets, coastal drives and some of Southern Maine’s best fall experiences. After a day of foliage, festivals and cider donuts, return to a thoughtfully designed room and sunset views over the Piscataqua River.
Plan your fall getaway to Kittery and experience the Seacoast at a slower pace.