A Perfect October Day in Kittery, Maine: Lighthouses, Lobster Rolls & Leaf-Peeping

As the crisp October air sets in and the leaves turn brilliant shades of red, orange, and gold, Kittery, Maine, transforms into a perfect fall getaway. Known for its famous outlet shopping, historic charm, and coastal beauty, Kittery offers visitors a mix of adventure, relaxation, and New England flavors.

Whether searching for fall foliage, exploring a lighthouse, or indulging in fresh seafood, this coastal town provides plenty of ways to soak in the season. Here’s your guide to making the most of an autumn visit to Kittery.

Since you are based out of Kittery, Maine, I’m concentrating on local areas within 20-30 miles in distance. Kittery, Maine, borders on Portsmouth, New Hampshire, as well, so some of my recommendations will be in NH as well.

*Note: I’m up on Benable, which is a new Pinterest-like platform. It currently has a waitlist to join, but if you would like to skip the line and move to the front, click this link and use my invite to make your first list. You may ask Why join Benable? Well, it also has the potential to pay you affiliate fees if someone clicks an item in your list and makes a purchase, and you also get a little sent your way. Nope, I haven’t seen a purchase off my lists yet, but it does send people to my art on Fine Art America, so to me, that is a win as well.

Fall Foliage & Outdoor Adventures

If you are arriving later in October (15- 30th), then you should have the roads “almost” to yourself. Most leaf peepers arrive early in October and head to Vermont and New Hampshire.

Best spots for leaf-peeping

Leaf Peeping along the coast is VERY different from being in, for instance, Smuggler’s Notch, Vermont, so you have to shake that image from your mind right now. There are few, if any, farmers’ back roads at the coastline to escape to.

I’m only going to say this once: I-95 is right there, but ignore the temptation to jump on the highway. Instead, I want you to look at Route 1 as a friend. Route 1 is one of the first roads created in America. It runs 2,370 miles (3,810 km) from Key West, Florida, north to Fort Kent, Maine, at the Canadian border, making it the longest north–south road in the United States.

Across the Piscataqua River from Kittery lies Portsmouth, New Hampshire, and you can visit the downtown area for all the dining opportunities as well as the museums, like…

Strawberry Banke Museum

Strawbery Banke is an outdoor history museum located in the South End historic district of Portsmouth, New Hampshire. It tells the story of a neighborhood called Puddle Dock. The settlers started building in this area in 1623 along the Piscataqua River and today the lovely homes and retail businesses allow you to experience early life in the colony.

Fort Foster and Fort McClary

Fort McClary predates the War of 1812 and is off Pepperall Road on Kittery Point. The cost is $4/person. You have a beautiful view of the Piscataqua River as it empties into the Atlantic Ocean.

Fort Foster was finished in 1901 and was for the defense of Portsmouth Harbor. Today, it costs visitors $25 per carload and there are trails and gun batteries to explore. There is a boardwalk extending out into the harbor from which you can view Wood Island Life Saving Station, and a bit further out is Whaleback Lighthouse.

The Marginal Way in Ogunquit, Maine (2.5-mile walk)

This trip is a measly 14 miles from Kittery so you will not be spending the day behind the wheel of your car. Ogunquit has at minimum 8 or more places to eat, and several of those are in Perkins Cove at the southern end of the Marginal Way.

This not-so-marginal way is a 1.25-mile-long cliff walk that winds its way from a starting point near the Sparhawk Oceanfront Resort on Shore Road and brings you south along a paved path, past stately hotels and inns, and rocky beaches to Perkins Cove at the southern end.

My suggestion to you is to wear comfortable walking shoes (it’s mostly all paved) and enjoy the views it provides, which are something to behold. There are 39 benches located at ideal viewing spots all along the path—perfect for sitting and contemplating the vibrant Atlantic Ocean.

Alfred Maine

For a little longer trip, you could plug Alfred Maine into your phone or car GPS. It’s 26 miles as the crow flies, or Google says 39 miles driving. Alfred is a picturesque little town with a great general Store. (Link to article on Alfred’s general store)

Unlike the tourist spots along the coast, where most of the hotels and eating opportunities spring up, towns like Alfred are places to escape to. You get away from high-end shopping, and there is just the general store and the Oak Street Bistro to grab a bite.

Kennebunk/kennebunkport

If you remember, we were talking about Ogunquit on Route One. If you continue north past that on Route 1 and you take Route 9, it will take you to Kennebunkport, another seaside town, but before you get there, you will first come to the Rachel Carson National Wildlife Refuge.

This nature preserve is a large salt marsh & estuary featuring hiking trails, woods & many bird-watching opportunities.

Lighthouses Near Kittery

If the weather is less than spectacular, you can stick to the coast. Three lighthouses are right nearby.

Portsmouth Harbor Lighthouse (1.8 miles)
- You could start by driving to Fort Constitution on where the lighthouse is on the edge of the Fort. You can go to New Castle and Great Island Common and view the lighthouse from there, and while you are there, you can see Wood Island Lifesaving Station and Whaleback Lighthouse.
Whaleback Light (Between 1 and 2.5 miles, depending on where you view from).
- As I said above, you can view this from Great Island Common Park, Fort Constitution, Fort McCleary, and Fort Foster (see above write-ups)
Nubble Light (5 miles as the crow flies)
- Nubble Light is one of my favorite lighthouses to go and view. It’s a very short drive, and while it is busy during the summer, in the fall it’s not too bad. It has a parking lot, and it can be dramatic if the ocean is kicking up. No matter what, it is sure to please.

Dining Recommendations

Lisa and I have only eaten at the Weathervane and Bob’s Clam Hut, and both are near the Kittery Trading Post.

Bob’s is like other clam shacks that Lisa and I like. It’s very informal. (Order at a window, take a number, and go have a seat until your number is called.

But there are many options for eating within a few miles of Kittery. Seafood & New England Classics (Robert’s Maine Grill, Warren’s Lobster House)

Breweries & Cafés (Tributary Brewing Co., Beach Pea Baking Co.)

Fun & Educational Stops

York’s Wild Kingdom (York, ME – 8 miles, ~15 min drive) – A small zoo and amusement park featuring animals, rides, and mini-golf.
Children’s Museum of New Hampshire (Dover, NH – 13 miles, ~20 min drive) – Hands-on exhibits, a giant dinosaur fossil, and a kid-sized town to explore.
USS Albacore Museum (Portsmouth, NH – 6 miles, ~10 min drive) – A real submarine that kids can walk through and explore.
Pumpkin Valley Farm (Dayton, ME – 25 miles, ~40 min drive) – Corn mazes, hayrides, and pumpkin picking.
Applecrest Farm Orchards (Hampton Falls, NH – 18 miles, ~25 min drive) – Apple picking, farm animals, and a weekend fall festival with live music.

Conclusion

Kittery, Maine, is a fantastic destination in October thanks to its vibrant fall foliage, crisp coastal air, and a perfect blend of scenic beauty and shopping appeal. Visitors can enjoy colorful drives along Route 1, explore the iconic Kittery Trading Post, and take in sweeping views of nearby lighthouses like Whaleback Light or the Nubble. But Kittery’s charm doesn’t fade with the leaves—year-round, it offers a dynamic mix of outlet shopping, fresh seafood, historic sites, and waterfront walks that make it an ideal stop for travelers in any season. Whether you’re leaf-peeping in the fall or browsing boutiques and enjoying lobster rolls in summer, Kittery delivers a quintessential coastal New England experience.

Jeff Foliage Folger

Autumn is a state of mind more than a time of year – Jeff Foliage

Visit my Amazon affiliate store for items that Lisa and I have curated for you. These items are either New England-made or things we think will make your fall foliage trip more successful.