Local's Guide: Maine Fall Road Trip Itinerary (New England)

Guest Post by Sara Williamson

MEET SARA

Hi y’all, my name is Sara Williamson. I am a photographer living in the Deep South with my husband & our two cats. We were both born & raised in Mississippi, but coincidentally both our dad’s jobs brought us to Maine when we were kids, long before we knew each other. Because of this we feel almost as at home in Maine as we do in Mississippi and decided to move there 2.5 years ago.

Maine is such a special place. You really can get the best of both worlds there: rocky coastlines and beaches and mountains and lakes. But the most magical thing about Maine by far is being there during the Fall. If you ever get the chance to see Autumn in Maine, take it! Even if it’s just for a weekend. And if you’ve only got a weekend, here’s a little Fall weekend road trip itinerary.

Maine is such a special place. You really can get the best of both worlds there: rocky coastlines & beaches + mountains & lakes. But the most magical thing about Maine by far is being there during the Fall.

Maine Fall Road Trip Itinerary day 1

Morning: Maine’s major airport is in Portland, about 50 miles in from the border of New Hampshire. Portland, Maine absolutely cannot be visited without seeing Portland Headlight. It is the most photographed lighthouse in the world! You’ve probably seen it on book covers and in movies before without even realizing it.

Spend some time exploring the rocks and ocean below or take a stroll through the gardens on the grounds. If you are there on September 11, Maine’s Open Lighthouse Day, you can grab a ticket to go inside the headlight which is not usually open to visitors. If you aren’t there for Open Lighthouse Day however, you can always visit the lighthouse museum nearby.

After Portland headlight, head to the Eastern Promenade for some breakfast from the food trucks and enjoy it with amazing views of the Casco Bay. Then head downtown to Portland’s Old Port and take a stroll through its historic streets.

Afternoon: Moving further North (about 30 minutes), make a stop in Brunswick, Maine. If you are visiting during October, walk down Maine Street and check out the Halloween window paintings by some of the students in the area. You can keep walking past the Mall, a park lined with food trucks that turns into an ice skating rink in the Winter! Continue on to Bowdoin College and enjoy the historic grounds and their campus art museum. If you make it to Brunswick before noon, there is a farmers market on the Mall and also down the road at Crystal Springs Farm. They have all kinds of vendors selling Maine goods!

If you’re in a hiking mood, check out Morse Mountain in Georgetown. It’s a great hike for those who want mountain and beaches in one! The other side of the mountain ends at Popham Beach, where the sand is soft and sparkly because of the quartz pigment in it. You can also check out my favorite lighthouse on your way there, Doubling Point light. It’s so cute and small! The sun really lights up the tall grass around it at sunset.

Evening: Finish the day in Freeport, Maine, about 15 minutes from Brunswick. This is home to L.L.Bean’s flagship location and is open 24 hours a day, 7 days a week. Take a picture with the giant bean boot, do some shopping (tip from a local: there’s an L.L.Bean outlet in the shops across the street from the flagship store!), and end the day with dinner at The Broad Arrow Tavern, located in the Harraseekat Inn. I recommend the clam chowder or lobster bisque. Book a room at the Harraseekat for the night to rest up for the next day!

Maine Fall Road Trip Itinerary day 2

Morning: Start your day by grabbing a coffee from Coffee By Design located in L.L.Bean (I recommend the caramel crème latte!) and hit the road to Bangor, Maine. Once you’ve arrived, head to 47 W Broadway to see the ultimate Fall abode: Steven King’s house. A lot of his horror stories are inspired by places in Maine and he lives those spooky vibes all year round in his home lined with an ornate iron fence decorated with iron spider webs.

Afternoon: After a pit stop by his house, make your way to Treworgy Orchard in Levant. This is the ultimate place to check off your Fall bucket list: apple picking, a corn maze, a pumpkin patch, and a general store that has apple cider and pumpkin donuts! There’s also goats and sheep to pet and feed on the grounds. It’s a great family friendly stop for all things Autumn.

Evening: Heading back South, stop in Camden, Maine. Get a room at the absolutely gorgeous 16 Bayview (where we spent our honeymoon!). Drop your bags, change into something comfortable, and take a hike through Camden Hills State Park. You can also drive straight to the top of Mount Battie and enjoy the Fall colors from an incredible vantage point.

Wind down the day checking out the shops around the hotel, or take a sunset schooner ride! On the schooner you’ll see Curtis Island Headlight and maybe even some porpoise or whales! Bring a jacket, the breeze coming off the Atlantic Ocean is chilly! Enjoy dinner on the water at Waterfront or Peter Ott’s, then tuck in for the night in the coziest rooms at 16 Bayview. If you’ve got an ocean view suite, you’ll enjoy some stunning views of the harbor and have a fireplace and free standing bath tub for ultimate relaxation. We loved spending the evening sitting on the balcony of our room enjoying a glass of wine & the ocean breeze.

When you are headed back to Portland the next day, you’ll be on Route 1 which goes through so many adorable & picture perfect Maine small towns like Wiscasett, Rockland, & Bath. It’s a great drive for leaf peeping as well!

Wrapping it up

Maine is truly a gem and 100% needs to be on your travel bucket list for Fall. I feel so lucky to have been able to live there and enjoy the state in its most magical season. We are back in Mississippi now, closer to family in these uncertain times during the pandemic. I love my home state with all my heart! But Fall in Maine is always on my mind. I hope everyone gets to enjoy this time in the Pine Tree State at least once in their lifetime!

THANK YOU!

Thank you, reader, for spending time on this post. We’re so glad you’re here and have more info for you in the sections below. And big thanks to Sara Williamson for contributing this piece of content to The Weithouse. Be sure to give her a follow on her social channels and check out her website. She is also a lifestyle and wedding photographer, and you can book her at the website link below.

Personal Instagram: @frecklesandfilm

Photography Instagram: @sarawilliamsonphoto

Website: www.sarawilliamsonphoto.com

STICK AROUND FOR A WHILE

Don’t be one and done. Check out our other great content we think you’ll love.

Want to explore more than just Maine? Read this blog post, where we share everything you need to know to plan a full New England road trip. Have Fall fever? Read our Airbnb roundups from some of our favorite mountain destinations, like Gatlinburg and Chattanooga.

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