Maine, Vacationland USA: Spilled Milk #312

My ultimate guide to Maine: where to stay, what to do, where to eat and when to go.

I’m partnering with USA Today to share my summer travel tips and recommendations for destinations across the United States. From Maine to Texas, we’re exploring my favorite restaurants, accommodations and things to do around the country.

I’ll also be cooking recipes inspired by each location and answering all your travel questions. There’s no paywall today, but you don’t want to miss a moment of our journey together—become a paid subscriber to Spilled Milk!

For the traveler who’s already eaten the lobster roll. And later in the week I promise we will have plenty of food-focused suggestions for you! This is a BIG drop, so be sure to keep scrolling for all things Maine.

There’s something about Maine in summer. The long golden twilights, the granite coastline veined with pine, the slow pace that begs you to stay a while. Let the crowds flock to the usual suspects—Bar Harbor, Kennebunkport, That One Lobster Shack With A Huge Line on Instagram. You’re looking for something else. Something wilder, more thoughtful. Here are 10 unforgettable ways to do Maine in the summer, beautifully and without cliché.

For what it’s worth, this is my EXPERIENCE in Maine. My father Robert Zimmern and his husband Andre LaPorte lived there for a decade at the end of their lives, I spent six summers there as a kid at Camp Moosehead in Raymond, Maine, and I still go back, so trust me, I know a little of what I am talking about here.

1. Brave the Knife Edge, Mount Katahdin
Summer is the only time you can reliably take on this legendary ridge walk, a harrowing and beautiful trail slicing across the peak of Maine’s tallest mountain. It’s a rite of passage for serious hikers—and not for vertigo sufferers. Plan, train and bring real boots. The reward? A primal, unforgettable view of Maine’s wild north.

2. Escape to Monhegan Island
Board a ferry from Port Clyde and arrive in another world. Monhegan has no cars, no pretension and no bad views. Hike dramatic cliffs, explore artists’ studios and spend the night at the historic Island Inn or a timeworn cottage where you’ll fall asleep to the sound of the sea.

3. Dine at The Lost Kitchen (If You’re Lucky)
Located in the tiny town of Freedom, The Lost Kitchen is one of the hardest reservations to land in America. If you get in, it’s a dream: candlelight, flowers, wood-fired fare and a menu that reads like a love letter to Maine. If not, visit the shop, roam the area and savor the countryside.

4. Antique Through Wiscasset
Maine’s best town for antiquing doesn’t scream; it seduces. Wiscasset offers elevated vintage finds and serious colonial charm. Think 18th-century sea captain homes, artfully curated shops and lunch by the water. Yes, there’s lobster—but maybe have the chilled cucumber soup instead. No, have both because Red’s is THE place to eat seafood in that town and DEFINITELY tell them I sent you. Seriously.

5. Summer on a Lake in Belgrade Lakes
Forget oceanfront crowds. Rent a lakefront Airbnb in Belgrade Lakes, where the vibe is loons at sunset and long swims before breakfast. It’s luxurious in its simplicity. Kayak at dawn, stargaze at night and live like you’re in a Richard Russo novel with better wine.

6. Cruise the Bold Coast National Scenic Byway
For those who want Maine without the crowds: drive north. Way north. This stretch from Milbridge to Lubec feels like a secret. Hike the cliff trails at Cutler Coast, wander windswept fishing villages and eat a lobster roll where the boat that caught it is still in sight.

7. Do an Oyster Crawl in Damariscotta
Summer is oyster season here. Tour the Damariscotta River by boat, where icy waters yield some of the best bivalves in North America. Slurp them at Glidden Point, visit OystHERS for a boutique raw bar experience and learn the backstory of each shell you lift to your lips.

8. Stay In a Design Cabin Along the Midcoast
Maine’s Midcoast is having a quiet design moment. Book a modern cabin between Belfast and Blue Hill. Think minimalist lines, giant windows and wildflower meadows. Spend days browsing indie bookstores, buying wine at Blue Hill Wine Shop and baking bread with Tinder Hearth sourdough.

9. Hike Cadillac Mountain for Sunrise (Do It Right)
Skip the crowds. Wake before 4 a.m., lace up and hike up Cadillac in the dark. Bring a thermos of Tandem coffee and a pastry from A&B Naturals. When the sun crests the Atlantic, it won’t be just another viewpoint—it’ll feel like a private ceremony between you and the planet.

10. Sunset Picnic Above Rockport Harbor
Grab a bottle from Maine & Loire in Portland before heading up the coast. Climb the small hill above Rockport Marine Park, spread a blanket and toast the sunset as schooners glide into harbor. Maine doesn’t get more romantic than this. And Rockport is a GREAT town to stay for a few days. My Dad used to stay there a few times a year. Unforgettable inns and superb places to eat.

This isn’t just Maine—it’s the Maine you really came for. Let the others chase T-shirts and chowder. You’ve got your own route.

Field Notes: Doing Maine Right

A cheat sheet for the discerning summer traveler

WHERE TO STAY

🛌🏻 The Longfellow Hotel, Portland
Portland’s most anticipated new arrival is a stunner: Nordic-minimalist design, a world-class spa (ASTRAEA), an elegant café-wine bar hybrid (Five of Clubs) and a location that’s walkable to both the West End and downtown. Refined, serene and effortlessly cool.

🏡 Browse architectural gems on Plum Guide and Airbnb Luxe. Look for properties in Blue Hill, Lincolnville, or Belfast for the best Midcoast design escapes.

🏖️ The Island Inn, Monhegan Island
Perched above the harbor with Adirondack chairs facing the sea, this inn is all coastal nostalgia with just enough polish. Ask for a room with a water view and prepare for the world to slow way down.

WHERE TO EAT & DRINK

🍽️ Tinder Hearth, Brooksville – Wood-fired pizza and perfect baked goods in a pastoral setting. Reserve early.

🍷 Blue Hill Wine Shop, Blue Hill – Natural wines, local cheeses and small-town charm.

🐚 Glidden Point Oyster Farm, Edgecomb – Shuck-your-own oysters with a river view. Bring a cooler.

🥘 The Lost Kitchen, Freedom – If you know, you know. Reservations are by annual lottery only.

🦞Red’s, Wiscasset – Lobster shack serving fresh seafood. Tell them I sent you!

🦪 OystHERS, Bath - Learn the backstory behind every oyster you eat at this raw bar.

🫐 A&B Naturals, Bar Harbor - Locally sourced products, including produce from nearby farms.

☕ Tandem Coffee Roasters, Portland - Single-origin coffee in a cozy cafe.

🍇 Maine & Loire, Portland - Natural wines from the Loire Valley.

🧀 State of Maine Cheese Co., Waldo - Artisan cheeses made on a fourth generation dairy farm.

EXPERIENCES TO BOOK

🛶 Damariscotta River Cruises – Tour oyster farms and wildlife-rich estuaries with a drink in hand.

🎨 Colby College Museum of Art, Waterville – A surprisingly world-class collection in central Maine. Free admission.

⛴️ Ferries to Monhegan Island – Depart from Port Clyde, New Harbor, or Boothbay Harbor.

WHEN TO GO

☀️ Mid-July through late August is peak summer glory. Book well ahead. For thinner crowds and golden light, early September is Maine’s secret season.