Travel + Discover Kittery: Maine Vacation Guide

Kittery cradles the interaction of the Piscataqua River and the wide-open Atlantic Ocean as the first stop in Maine across the I-95 bridge.

Arguably Maine’s oldest town, and Kittery is now edging closer to its 400th birthday. It’s also home to the nation’s oldest continuously operating Navy yard.

If you think Kittery is just about shopping at amazing outlets, we’ve got some surprises in store for you. The collection of peninsulas means many nooks and crannies to explore, each offering unique natural surroundings and a heaping dose of history.

A Look Back at Kittery’s Story (It Goes Way Back!)

Long before Kittery became Maine’s oldest town, the Abenaki people lived along its rivers, drawn to the rich fishing waters and dense forests.

When English settlers arrived in the 1600s, they recognized the same advantages – deep harbors, abundant timber, and access to the Atlantic – making it an ideal shipbuilding hub. The town played a role in the Revolution, and the Portsmouth Naval Shipyard kept it thriving.

Today, that shipyard helps protect America by maintaining nuclear submarines. Despite a boundary dispute, the U.S. Supreme Court finally realized what we all knew – it’s on the Maine side of the state line.

Tucked in the Corner of Maine

You can’t miss the exit right across the state line from New Hampshire, across the water from Portsmouth. Kittery is about an hour from Boston and 45 minutes from Portland by car. Don’t wait until you hit the outlet mall to exit. Take exit 1 or 2 to see the real Kittery.

Getting Your Bearings in Kittery

Getting around Kittery means crossing or navigating a car around the waterways. Here’s a quick breakdown of the neighborhoods.

• Badger’s Island – This small island in the Piscataqua River is technically part of Kittery but feels like a transition zone between Maine and New Hampshire. It has waterfront restaurants and marinas.
• Kittery Foreside – The town’s historic and commercial hub, just across the river from Portsmouth, NH. It’s as close to a downtown area as you’ll get in Kittery.
• Kittery Point – A scenic, residential area that extends south along the coast. It includes Fort McClary, Pepperrell Cove, and the secluded Seapoint Beach.
• Cutts Island – A quiet, wooded peninsula with nature preserves, trails, and marshland.
• Route 1 / Outlet Area – A commercial strip with the well-known Kittery Outlets.
• Gerrish Island & Chauncey Creek – A residential and natural area mostly known for the Chauncey Creek Lobster Pier and Fort Foster State Historic Site.

Beach Day in Kittery? You Might Be Pleasantly Surprised

Yes, but you have to know where to look. Be advised – it’s not the long stretch of sandy beaches you’ll find in places like Wells, Ogunquit, and Old Orchard Beach.

At the same time, you won’t have to deal with the crowds you’d face in those other places when you visit these beaches:

• Pier Beach (Fort Foster)
• Horn Point (Fort Foster)
• Scuba Beach (Fort Foster)
• Crescent Beach
• Seapoint Beach

The Fort Foster beaches are the easiest to access. Those heading to the Crescent or Seapoint Beaches should consider biking there. Parking is limited and only for residents with a town dump sticker affixed to their cars.

Always check the water quality conditions before visiting a beach in Maine.

Did You Know Kittery Has Islands? Let’s Explore Them

Not all of Kittery is on the mainland. About 5 miles offshore is the Isle of Shoals. Here, you’ll find retreats like Appledore Island, Smuttynose Island, and Cedar Island. The other half of the islands are across state lines in New Hampshire.

Limited tours are available through the University of New Hampshire and depart from New Castle, NH. To get into the spirit, try reading some of Celia Thaxter’s essays and poems, as she lived on the island for many years.

DID YOU KNOW? The infamous pirate Blackbeard is believed to have hidden a treasure on Lunging Island at the Isle of Shoals.

A Little Bit of This, a Little Bit of That | Kittery Has You Covered

Kittery is a town with four seasons of things to do and places to visit. Even during the off-season, very few places close down.

Kittery Historical & Naval Museum

You can’t visit Portsmouth Naval Shipyard without the right security clearance, but the Kittery Historical & Naval Museum still gives a heaping dose of marine and wartime history.

The tour is self-guided, and there’s a scavenger hunt for the kids. The museum is open year-round, but make an appointment between mid-November and March.

Fort Foster Park

Fort Foster Park is one of Kittery’s best spots for coastal views, history, and outdoor space. Originally a military defense site, it’s now a public park with walking trails, rocky beaches, and old fortifications to explore.

The views of Portsmouth Harbor and Whaleback Lighthouse are worth the visit.

Fort McClary

Fort McClary State Historic Site is a small but interesting site overlooking the Piscataqua River. Built for coastal defense and used during five wars, it has a mix of old stone structures and wooden buildings that can be toured.

The hilltop location gives great views of the river and Portsmouth.

Cutts Island Trail

Cutts Island Trail, part of the Rachel Carson National Wildlife Refuge, takes you through a loop of forests, tidal creeks, and marshland. The easy 1.8-mile loop makes for more of a stroll than a hike. However, you’ll get to see wildlife and stretch your legs after a long car drive.

If you like this trail, consider the Brave Boat Headwaters’ 60-acre parcel nearby.

Wood Island Life Saving Station

I always get goosebumps when I write about the men who lived by the motto, “You have to go out, but you don’t have to go back.”

You’ll learn about these brave men who served at Wood Island Life Saving Station. Before there was the Coast Guard, the Life Saving Stations were the rescue groups that helped shipwrecked sailors find their way to land.

Please note that this boat tour departs from Portsmouth, but the island is in Kittery.

The Dance Hall

When the sun goes down, The Dance Hall heats up. Right in the heart of Foreside, this lively venue boasts music from various genres throughout the year. Even better? It’s an all-ages dance party in a historic venue dating back to 1928.

Kittery Premium Outlets

By the time you get to Kittery Premium Outlets, renovations will be finished. The collection of more than 50 shops keeps bringing in new tenants. It’s a big enough mall to spend half a day but not too large that you’ll literally drop after you shop.

If you’ve read that the outlets are being demolished, that’s a much smaller shopping plaza that was known as the Outlets at Kittery. A new hotel is expected at that site in the coming years.

Kittery Trading Post

As one reviewer put it, the Kittery Trading Post is like “Cabela’s on steroids.” In a state known for L.L. Bean’s flagship store, this shopping area does just fine. In addition to three stories of sporting goods, clothing, home goods, and snacks, there’s a stuffed moose greeting you on the way in.

Seacoast Maritime Charters

Skip the sold-out scheduled tours of the other Maine seaside towns and book your own trip through Seacoast Maritime Charters. The year-round charters include space for up to 50 of your closest friends. Trips can go around the coast or to the Isle of Shoals.

If you’re looking for something a little less expensive, consider the Star Island Mailboat trip.

Take Flight Aerial Adventure Park

Climb, zip, and balance your way through 65 challenges at Take Flight Aerial Adventure Park. Each visit starts with a safety lesson before guests climb their way to new, challenging heights. Two zip lines and an ax-throwing option make it a fun way to spend the day in Kittery. Open seasonally.

Cozy Cafés, Fresh Seafood, and More | Let’s Talk Kittery Food

One of the fun parts about dining in Kittery is that grabbing a bite becomes a mini adventure. Instead of having all the restaurants grouped into one area, you can explore Kittery’s landscape by sampling the best options around town.

Bob’s Clam Hut

The list of accolades for Bob’s Clam Hut is almost as long as its menu. This Kittery staple is approaching 70 years of service with a convenient location right off Route 1.

While clams steal the show, the menu is filled with Maine seafood, burgers,  hot dogs, and heaping doses of sides.

If you’re into celebrity recommendations, Martha Stewart and Guy Fieri are both big fans of Bob’s Clam Hut!

State Line Lobster Co. 

One of the newest restaurants in Kittery claws its way to Route 1 at Stateline Lobster Co. Check out the Facebook page for opening dates and the robust seafood-filled menu. You don’t even have to worry about finding an ice cream shack because that’s on the menu, too!

Frisbee’s Wharf

Whether you arrive by car, boat, or bike, Frisbee’s Wharf in Pepperrell Cove offers a scenic view to sit and enjoy locally sourced seafood.

Snag a spot in the outdoor seating area, and splurge on a seafood tower, or pick a lobster made your way. Lazy man or in the raw, the lobster dish with a view will have you considering a move to Maine.

Reservations are strongly recommended.

Robert’s Maine Grill

Another of Martha Stewart’s favorites is Robert’s Maine Grill. It offers Maine classics like lobster and chowder, as well as specialty dishes like baked haddock and steak. You can sit inside or order to go.

Board. Wine, Cheese, and Charcuterie

Board. Wine, Cheese, and Charcuterie serves creative combinations of charcuterie platters in a refined setting paired with a wide range of wines. Choose from the menu, or create your own. The flexible menu is equally suitable for romantic and family dinners.

The Black Birch

Explore the fine dining side of Kittery’s Foreside District at The Black Birch. The menu veers from lobster rolls and clam buckets to a versatile menu, including brick chicken and poutine and duck confit.

The menu includes small, medium, and large plates, offering something for everyone, no matter how hungry you are. You can’t make reservations here, but the scenery outside makes the wait well worth it.

When Pigs Fly Pizzeria

Come hungry as a hog to When Pigs Fly Pizzeria because the menu is so much more than just basic pizza. The brick oven pizza specialties make up just a small section of the menu. Plus, there’s a selection of grab-and-go artisan breads, ale house specials, and a company store.

Don’t Miss Kittery’s Sister City

Kittery and Portsmouth share a watery border, and there’s a lot to do on that side of the Maine state line. Plus, New Hampshire has no sales tax. Pick up your staples while exploring before you go on a shopping spree in Kittery.

As a bonus, some of the pictures of Kittery’s coastline can be taken from the New Hampshire side!