Travel

A FALL TRAVEL GUIDE TO COASTAL MAINE

The Steele Maiden: Travel Guide to Coastal Maine

I’ve already shown you what I wore on our trip to Maine (here, here and here), but I’ve been bursting to tell you more about all of the great things we saw and did. Oh and ate. Without further ado.. my fall travel guide to coastal Maine.

The Steele Maiden: Travel Guide to Coastal Maine

While I’ve been to Maine in both Summer and Winter as a kid, I had never been in the peak of Fall and now I don’t think I’d want to go at any other time. The middle of October (depending on the weather that particular year) is going to allow you peak leaf peeping and temperatures that are crisp but not yet truly cold. This trip is best enjoyed by car as so many of the towns are just a short 20-30 minute drive from one another. Allowing both scenic coastal drives and multiple stops within a single day. We saw most of south/mid-coast Maine in just 3 1/2 days. I suggest starting at Nubble Lighthouse just outside of Ogunquit and ending with Bar Harbor and Acadadia National Park.

The Steele Maiden: Travel Guide to Coastal Maine

While it probably goes without saying, you’re going to eat Lobster while in Maine. And it’s going to be gooooood. It’s offered in nearly every variety but as you pop from town to town a lobster roll from a seaside stand is an experience not to be missed. We loved the Clam Shack in Kennebunkport and Red’s Eats in Wiscasset. But don’t think your dining is going to stop at lobstah (as the locals say). We were pleasantly surprised by the amazing food options we found throughout our trip. Standouts include an unforgettable dinner at Earth at Hidden Pond outside of Kennebunkport (make reservations in advance and request a seat near the fireplace!), Duckfat (don’t miss the truffle fries) & The Holy Donut (their chai tea donut was possibly the best donut I’ve ever had) – both in Portland. P.S. While you wait for your table at Duckfat, walk over to Shipyard Brewery for a quick beer flight of local craft brews.

The Steele Maiden: Travel Guide to Coastal Maine

One of our favorite activities while exploring Maine was touring the coast’s lighthouses and sightseeing all of the gorgeous historic homes. We checked out Nubble Lighthouse near Ogunquit and Portland Head Light in Cape Elizabeth (the cliff walk nearby was another favorite activity!). While we spotted beautiful homes in almost every town we stopped through, the houses in Kennebunkport and Wiscasset were some of the most charming I’ve ever seen. Look closely for the door markers on the homes to see the year in which they were built and often times the name of the original owners.

The Steele Maiden: Travel Guide to Coastal Maine

Admittedly I didn’t do much shopping while we were on this particular trip, but Kennebunkport was dotted with cute boutiques and Portland had a strong small shop vibe that I loved. My favorite stores downtown were Portland Dry Goods (think luxe lumberjack for both men and women) and K Colette for home goods with a chic nautical-inspiration.

The Steele Maiden: Travel Guide to Coastal Maine

Have more questions about what to see or where to go? Feel free to ask below in the comments or contact me directly here.

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WISCASSET, MAINE: FALL OUTDOOR STYLE

The Steele Maiden: Fall Outdoor Style in Wiscasset Maine

On our last day in Maine, Adam and I made a plan to drive up the coast to Boothbay Harbor but along the way passed through a small town called Wiscasset and couldn’t help but pull over the car. From the most charming historic homes (each had a date marker by the front door and most were built in the late 1700s through early 1900s) to beautiful scenic seaside landscapes (those Fall colors though…) it was easily one of my favorite American towns I’ve ever visited. I wore easy and comfortable separates (a quilted primaloft jacket and striped scarf for the win) for an afternoon exploring outdoors.

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PORTLAND, MAINE: STRIPED TURTLENECK AND OVER THE KNEE BOOTS

The Steele Maiden: Downtown Portland Maine wearing striped turtleneck and over the knee boots

Blame it on October and maybe the fact that downtown Portland reminded me a little bit of Salem.. but I guess I was channeling witchy woman vibes with this striped turtleneck, black over the knee boots and bomber jacket (it’s the reversible one that I last wore on the polka dot side here).

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KENNEBUNKPORT, MAINE: CLASSIC FALL STYLE WITH LANDS’ END

The Steele Maiden: Classic New England style with Lands' End in Kennebunkport, Maine

I’ve been itching to go to the seaside town of Kennebunkport for ages and so when I started planning our Maine road trip – I knew it had to get it’s fair share of time to explore. The town certainly didn’t disappoint. Full of classic New England charm (don’t worry, I’ve got a big travel guide coming soon!), I went with an equally classic outfit to match.

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VISITING PORTLAND HEAD LIGHT IN FALL LAYERS WITH TALBOTS

Visiting Portland Head Light in Cape Elizabeth Maine wearing Talbots fall layers

And just like that – our vacation came and went. Adam and I spent the past several days road-tripping up the New England coast and exploring Maine. On our second day of the trip, we started off in Cape Elizabeth at Portland Head Light. Since weather was full out Fall up north (and windy by the ocean), I packed practically in light layers and cozy textures.

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Fashion, Travel & Lifestyle. Based in NYC.