The ultimate fall weekend on Maine's southern coast

Sometimes, when things seem bleak and I’m feeling blue, I like to book a trip to somewhere I've always wanted to go. It was in this spirit that I escaped to the coast of southern Maine in New England for a weekend of long walks, delicious food, charming towns and hanging out with my beloved bestie, fellow travel writer, Rebecca. 

While Maine can be unforgivingly chilly and dank when the weather turns cold, especially along its windswept coast, this weekend served up late fall perfection. But honestly, I’d recommend visiting Maine at any time of year – just pack the right clothes, and get yourself to its friendly towns and stunning shoreline.

• When to arrive: I took Friday off to fly up to Portland for the weekend – a one-hour flight from New York City. My travel buddy flew in from Miami and had to connect, but there were several options and it was a smooth trip. To maximize our time in Maine, we stayed through till early Monday morning.

• How to get from the airport: Rent a car from the airport as you'll be driving south for about an hour to reach your first stop in Ogunquit.

• Getting around town: As in many parts of the US, you’ve got to drive to get everywhere, but it's easy to find parking in each town or hamlet so you can explore on foot.

• Where to stay: There are any number of charming B&Bs and inns in Ogunquit, but for this trip, I wanted to stay somewhere special. I picked somewhere that has long been on my list – the lovely Cliff House toward Cape Neddick.

• What to pack: Bring appropriate gear for the local climate. In early November this meant layers – shirts, sweaters, jeans and casual pants, a jacket, hat, scarf and gloves. We also packed party-ish outfits for a night out at a local piano bar.

Friday: Portland to Ogunquit, with seafood sandwiches and margaritas

Morning: We arrived in Portland around midday, renting a car at the Portland Jetport – one of my favorite smaller airports in the USA. Then we hopped onto Route 1 for the drive south to Ogunquit.

How to spend the day: On arrival at Cliff House, we chose valet parking ($26) for the car, only to realize that self-parking was just as easy - whoops! We entered a lobby full of drama, with comfortable couches around a lit fireplace and floor-to-ceiling windows framing the sea view. The hotel’s perch atop Bald Head Cliff makes you feel like you’re at the end of the world, just with plenty of amenities and luxuries close at hand.

After check-in, we explored the property and got a little lost because the halls of Cliff House are labyrinthine. Walking around the extensive grounds, we watched large groups of sea ducks (harlequin ducks, perhaps?) bobbing on the water, and marveled at the Kittery Formations threading through the bedrock of the cliff. I wished I knew a geologist who could explain the geological background of this striking coastal landscape because it was amazing to behold.

Dinner: We started early with a drink – a martini for me, a glass of Sauvignon Blanc for Rebecca – at around 5pm in the Tidemark Lounge, adjacent to The Tiller, the hotel's fancy dining room. Floor-to-ceiling windows framed the view as a staffer lit the fire and a musician set up his mic and amp. It was a moment of all-round loveliness.

We decided to keep things casual on night one, so we went to the hotel's cozy seafood spot, Nubb's Lobster Shack. I ordered a tuna melt and my dining companion ordered a crab cake sandwich. Both hit the spot. We also split a bowl of clam chowder and decided to up the ante with a round of margaritas, because, well, why not? 

After dark: We decided to turn in early because our room was gorgeous – inviting and so comfy, with an incomparable ocean view, a balcony with two chairs, an indoor sitting area and two of the most comfortable king beds we had ever slept in. Once settled under the covers, we agreed we might never get out of bed again!

Saturday: waterfront walks and window-shopping in Ogunquit

Morning: After a deep night's sleep, we coaxed ourselves out of bed and drove to Ogunquit, about 10 minutes north of the hotel. We weren’t starving, so we decided to get a coffee and a pastry in town, and happened upon Mornings in Paris, a tiny coffee shop with only 4 small tables. Cappuccinos, croissants and banana bread set us up perfectly for the day.

How to spend the day: Fortified with caffeine and carbs, we walked around town, absorbing the off-season vibe. Ogunquit is primarily a summer resort, so some stores and restaurants were closed, and the streets were quiet, even though there were still a handful of people walking about. We enjoyed some window shopping and were lured inside Ciao Candle Bar and Boutique by an adorable lobster baby onesie in the window. They also offer DIY candle-making sessions for people looking for that made-it-myself touch.

Our main (ahem) objective for coming to Maine was to walk the Marginal Way – an experience recommended by my colleague Laura Motta in her summer travel guide to Maine.  But we first strolled over to Ogunquit Beach, which had a lovely covered sitting area decked out with Adirondack chairs. Even though it was moist and chilly, there were plenty of beach walkers and a family playing football, setting a friendly mood.

The paved footpath known as the Marginal Way winds along the rugged coastline for 1.25 miles, providing extraordinarily beautiful views of the sea, wave-lapped coves, rock formations and some interesting flora and fauna. Even in the winter low season, it was fairly busy, which made me wonder how crazy things must get in the high season. It took us about an hour to walk the length of the path to Perkins Cove and about half that to get back because we didn’t stop every five seconds to gawk at the view. 

We rewarded ourselves with two of the best, most generously stuffed lobster rolls we had ever eaten. Two of the lobster shacks on our wishlist were closed for the season (despite claims to the contrary on Google) but Footbridge Lobster was open, with a sign above its door proclaiming that this is “where locals get lobster rolls.” The no-nonsense, parking-lot-side shack had no seating, but there were plenty of benches nearby, lending the experience an agreeable fishing village vibe.

Dinner: After more walking and exploring the area in the afternoon, we worked up enough of an appetite for a drink and a bite or two. We’d heard good things about The Front Porch Piano Bar & Restaurant, and it did not disappoint. Live music, a tasty menu (we rated the wings and the mussels), a rowdy crowd and excellent cocktails were the ideal formula for a rocking Saturday night out in Ogunquit. However, having started early, we were finished by 8pm and returned to Cliff House for an early night.

Sunday: brunch, more beaches and another iconic Maine town

Morning: Our Sunday morning coincided with the end of daylight saving time, so we got an extra hour of sleep, and we couldn’t have woken up feeling more refreshed. There was a coffee and water station on every floor of Cliff House, so we were able to enjoy a freshly brewed cup of coffee on our balcony, wearing the hotel’s plush checkered bathrobes and slippers. Is there anything more sublime than sipping hot coffee on a chilly morning whilst looking at the ocean? 

After a leisurely start, we enjoyed a blindingly bright Sunday brunch at The Tiller, watching the sunlight dance on the ripples of the sea from the exceedingly lovely, serene dining room. Eggs benedict and crab chorizo breakfast burrito were both totally delicious. Then we walked around the property again to marvel at the views and take more photos. 

How to spend the day: We decided to drive up to Kennebunk to walk along the beachfront and ogle at historic summer homes we knew we could never afford. Then we drove on to enjoy some late fall foliage in Hope Woods & Cemetery, following an easy 2-mile hiking trail (more of a woodsy walk) that we found on AllTrails.

We were too near Kennebunkport not to swing by, so we motored slowly through town. I had hoped to peek inside St Ann’s Episcopal Church, a historic stone chapel with stained glass windows from the late 1900s, but we pulled in to find the door locked (thanks again, Google). As we were getting back into our rental car, we noticed a line of official-looking cars slowly inching past. I thought we were in some kind of trouble until I realized we were parked next door to the Walker's Point Estate – the summer holiday retreat of the Bush family!

After our Kennebunkport jaunt, we drove back to discover a courtesy charcuterie plate waiting for us at the hotel, as well as a lovely bottle of Pinot Noir. We turned on some NFL football and had a bit of an in-room picnic with cured meats, cheese, fruit, crackers and wine – accompanied by more stunning views of cliffs and ocean. The perfect Sunday afternoon!

Dinner: Rebecca spotted lobster fried rice on the dinner menu at The Tiller, and they kindly let us order that to eat at the bar. We devoured it, along with more wine, before retiring to the lounge to stare at the cozy glow of the fire. 

After dark: Our morning wake-up call was booked for 4am, so we called it an early night. Then, on the way to our room, we remembered that the hotel had its own adorable little movie theater. The tiny marquee listed The Perfect Storm as the night’s feature, so we peered in and watched about 10 minutes of the movie before we remembered how the story unfolded and left.

Monday: leaving Ogunquit

It still felt like nighttime when we got into the car at 4:30am the next morning to drive to the airport in Portland, but we were refreshed by our trip. We had the most relaxing, lovely getaway and made a pact to return to Maine for another fall weekend next year. Indeed, I'd recommend a visit to Southern Maine to anyone at any time of year!