If you've ever driven into Maine, you probably know the feeling. You cross the Piscataqua River Bridge, the river opens up beneath you, and the "Welcome to Maine" sign comes into view. Vacation suddenly feels official. A minute later, you're in Kittery.
For a lot of visitors, that's where the story ends. They continue toward York Beach, or another Maine destination, without giving the town a second thought.
Trust us on this one. Don't be in such a hurry.
Just fifteen minutes from Anchorage Inn, the town of Kittery is full of history, local shops, waterfront views, fresh seafood, and enough small-town charm to fill a morning or afternoon. Better yet, you'll still have plenty of time to head back to York Beach before the day is over.
If you've ever wondered, what is the oldest town in Maine? The answer is Kittery.
English settlers established roots here in 1623, and the town was officially incorporated in 1647. To put that into perspective, it happened more than 125 years before the United States even existed.
Indigenous peoples lived throughout this region for thousands of years. This was long before European settlers arrived. The area was known as Amiciskeag, an Algonquin name translated as "fishing point," a reminder of the waterways that have shaped life here for centuries.
In some cities and towns, history is displayed inside museums. But not here. It’s fully a part of the landscape.
Walk through Kittery Point, and you'll find centuries-old homes, historic landmarks, and streets that show the town's maritime heritage. The oldest house in Maine still stands in Kittery, and it's one of many reminders that this town’s history is right there, on full display.
Drive into Kittery on Route 1, and you're following one of Maine's oldest roads. This route was part of the original King's Highway, a colonial route that connected coastal communities long before modern highways existed.
That's what makes Kittery different. Its history isn't something you read about before your trip. It's something you experience as you explore.
One of the best things about Kittery is that you can explore a handful of well-chosen stops and easily fill a memorable half day.
Start in the Kittery Foreside, the town's quaint downtown, where local boutiques, bookstores, coffee shops, and art galleries create an easy pace to slow down for a while. Grab a cup of coffee, browse a few locally owned shops, and simply enjoy wandering the streets.
The Foreside has also become one of the most talked-about food neighborhoods on the southern Maine coast, and much of it is independent and locally owned. Within just a few blocks, you can find Italian, American, Asian, and Indian restaurants, so it's easy to build a meal around whatever you're in the mood for. Tulsi, the neighborhood's North Indian restaurant, has earned national recognition for its cooking and is a local favorite worth seeking out.
Of course, many visitors also make time for the legendary Kittery Trading Post. Outdoor enthusiasts have shopped here for generations, and it's one of those places that's just plain fun to explore.
If shopping is on your agenda, the Kittery Outlets offer everything from national brands to specialty retailers. Here's a local tip: mornings usually bring lighter crowds, which makes it a much more relaxed experience.
When you're ready to trade shopping for salt air, head out to Fort Foster on Gerrish Island in Kittery Point. There's a per-car fee in season, and it's worth it: historic coastal forts to explore, nature trails, and a playground for the kids. Best of all is the beach, where low tide opens up some of the best tide pools around.
A great local stop afterward is Chauncey Creek Lobster Pier, a seasonal lobster pier on a tidal creek in Kittery Point. You order freshly steamed lobster at the window and settle in at a colorful picnic table over the water, but everything else you bring yourself. It's a bring-your-own spot, so pack your own drinks, salad, and charcuterie. Locals go all in, arriving with tablecloths and candles to dress up their table. Craving fried clams instead? Bob's Clam Hut has had a line out the door since 1956.
One reason Kittery works so well is that it doesn't require an entire day.
Head over in the morning, especially if you plan to visit the outlets before they get busy. Spend some time exploring the Foreside, browse the shops, and grab lunch at a local spot. From there, head out to Fort Foster for the forts, the trails, and some time on the beach hunting for tide pools. When you're ready to eat again, Chauncey Creek is right nearby for a relaxed, bring-your-own lobster dinner on the water.
Simple. That's really the beauty of it. You don't have to rush from one attraction to the next or worry about fitting everything into a strict schedule. Kittery is the kind of place where a slower pace is encouraged.
By mid-afternoon, you can be back at Anchorage Inn, ready for a few hours at Long Sands Beach, an evening stroll, or dinner overlooking the water.
One of the advantages of staying at Anchorage Inn is how easy it is to explore beyond York Beach while keeping the hotel as your home base.
The drive to Kittery takes about fifteen minutes. It’s one of the easiest day trips in the area. You can experience the oldest town in Maine, browse local shops, visit historic landmarks, and enjoy fresh seafood without spending hours in the car.
Then it's back to the beach.
So the next time you cross the Piscataqua River Bridge and officially arrive in Maine, consider making one small change to your plans. Pull off Route 1. Spend a few hours in Kittery. We have a feeling you'll be glad you did.
Book your stay at Anchorage Inn and discover how easy it is to experience York Beach, Kittery, and the very best of southern Maine.