The ultimate weekend in Southern Maine: falling for Ogunquit in fall

09.12.2024 - 19:21 / lonelyplanet.com

Dec 9, 2024 • 9 min read

Sometimes, when things seem bleak and I’m feeling blue, I like to book a trip to somewhere I know will turn my frown upside down. 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, and 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.

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