Scenic Drive Traveling Maine's Coast To Boston In The Fall// 7 day Maine Itinerary

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Fall has always been my favorite season. The time when everything bursts with its last beauty, as if nature had been saving up all year for the grand finale.
— Lauren DeStefano
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On November 1st Lin and I landed in Bangor Maine to travel the coast down to Boston. This trip had been on my bucket list as long as I can remember and I am so happy that we followed through. Maine’s Route 1 road trip is as quintessential New England as the West Coast’s Route 1 drive is classic California. While this itinerary starts from Bangor Maine and heads down the coast to Kennebunkport, it can certainly be enjoyed in the opposite direction too. There are two ways to go about this ride: Make a lot of stops on the way up and then power home. Or, pick a few pit stops for the way up, and save a few for the way back. There are so many various options.

A lot of planning went into my itinerary and I really hope you enjoy seeing Maine’s beautiful coast through my eyes—the must-see’s and must-do’s and the amazing culinary scene…OMG. This was such an incredible 7 days and I will forever remember every second of Maine’s endless cute towns and all the lobster rolls!

Please also note due to Maine having unseasonably warm temperatures, we got there just in time to see lots of fall foliage. Had we gotten there a week earlier though we would have really made it’s peak. Many of the restaurants we wanted to check out had already closed for the season too a week prior. So just watch the weather patterns to plan…all though I would imagine things just keep warmer and warmer so naturally the season will start later and later in Maine. But who really knows for sure?! HA! I would also add another 4 or 5 days in a perfect world. I will just have to go back and I am not complaining about that one bit! Hear that Maine Tourism?! A summer trip on the back of a motorcycle just might be calling my name.

DAY 1: Hancock village Maine:  STAY AT Ironbound Inn

We flew into Bangor from Oklahoma and of course, nothing is direct so I always plan a full travel day here. We arrived in Bangor and rented a car and headed down to Hancock, located on the mainland at the head of Frenchman Bay. This legendary property is located on US Highway 1, in the village of Hancock, Maine. It is 10 minutes east of Ellsworth; and a 35 minute drive from the Bar Harbor/Acadia/Mount Desert Island region. Yes, a bit off the beaten path, but well worth the experience. We arrived after 6 p.m and got settled in and enjoyed a delish dinner at The Ironbound Restaurant. The casual dining rooms are of an old world charm, where a large fireplace welcomes you into a casual, thoughtfully decorated space. They are about locally sourced foods, fresh fish and quality meats. Fresh Maine oysters are available and are hand-shucked to order. Highly recommend the Haddock soup, and of the fresh dinner salads, the scallops, and the lobster mac and cheese! They have a well stocked bar that offers spirits, fine wines, local brews and drinks crafted with fresh fruits and house-made mixers. They make a mean filthy martini with house made blue cheese olives !! Adjacent to the bar is The Sitting Room, where comfortable couches and furniture are a great place to stop in for a drink to gather with friends or to meet other travelers. It’s truly a gem here! And we feel so fortunate that we made it on the very last night before they closed for the winter season. (they reopen in May if you happen to have stumbled on this deep in the Winter season)

We also had a lunch at Ruth & Wimpy’s which is a tad more touristy but we enjoyed it.

(Chippers Restaurant also came highly recommended. We were not able to get in so make a reservation and report back)

Then it was time for an early slumber as we had a full day of exploration the next day!!!

Day 2: Acadia National Park/Bar Harbor

So we opted to stay in Hancock one more night originally and just take a day trip to Bar Harbor and Acadia National Park. If I could do this trip again though..I would stay in Bar Harbor on night 2. (see you lucky ducks..I make it easy for ya’ll) But really you cannot go wrong either way!

Okay so this was one of my favorite days of the whole trip and one of my favorite days of my entire life really.

You will pass the cutest Happy Clam Shack on the way!!! Of course you should take a pic because it’s such a #MaineThing.

We arrived in Bar Harbor early and had breakfast at Jordan’s. We adored this local, home-style restaurant so much! You must try the famous Maine wild blueberry pancakes. Thank me later by buying me the mix they sell with the blueberry syrup. We then headed to Acadia National Park. You will want to plan a few hours here driving the Park Loop. In the Spring and Summer I would definitely rent bikes and take a ride on the famous Carriage Trails (45 miles of interconnected car-free gravel roads), and enjoy the delicious hot and steaming popovers at the Jordan Pond House.  (closed for the season when I was there) Acadia’s views are pure magic, especially in the fall. I loved Sands Beach. The day we visited, it was soooo cold and windy and foggy and just perfect Sam weather. Most of the Maine coast is rocky and cliffy, which makes this small, inlet, ocean shore Sands Beach stand out—and I could live there! It’s a gelogic rarity-one of the few cold water shell-based sand beaches in the world. It’s nestled between mountains and rocky shores on the east side of Mount Desert Island. Head up to Cadillac Mountain too. Many locals catch the sunrise there half the year. Due to the fog and the Gail force winds, we had zero visibility so I was not able to shoot anything there.

After you explore Acadia, head back to Bar Harbor to enjoy the bustling downtown area. There are so many locally owned shops and eateries and bars! I highly recommend an afternoon blueberry beer and a cup of New England Clam Chowder at The Thirsty Whale. Get the side of garlic bread too for the soup-bread is such a game changer with clam soup in my opinion.

Day 3,4, and 5: Portland Maine: Stay at Pomegranate Inn or The Press Hotel

We hit the road early to meet family in Portland for lunch! We would stay here for three nights…and Portland is so rad but if I could do it over again, I would two nights here and extend my time in Cape Elizabeth or Kennebunk Port which we will talk about shortly!

Portland is the city where you can smell the ocean while you’re shopping at small local businesses, while eating your heart out. There’s been somewhat of an artist and food renaissance in Portland in the past few years, adding to the list of reasons to visit. Bon Appétit published an article on its website that declared Maine’s largest city the 2018 Restaurant City of the Year. Deputy editor Andrew Knowlton wrote the article, which says the “sheer number of outstanding openings” in the city have made it the top food destination in the country this year. Knowlton previously declared Portland “America’s Foodiest Small Town” in a 2009 article for the same magazine. And it is no joke. Love to eat? Love to drink? (love beer?) Portland is your place!

Old Portland is so charming with it’s cobblestone streets too! (do not wear heels)

Where I Would Eat & Drink in Portland, Maine 


Tandem Coffee: Tandem has two coffee spots in Portland: A café in East Bayside (open weekdays only) and a more bakery-focused spot in the West End, near The Danforth (open every day). They have the best scones and I do not even like scones. I am STILL dreaming about the spicy molasses +ginger cookies too. And the loaded biscuits..OMG the loaded biscuits!!! We visited three times!!! I met the amazing John Sundling there too from Plant Office. His wreaths are stunning. I even brought one home with me! HA! The coffee is a bit too bright for my taste but I could eat scones and cookies here everyday.

The Holy Donut: These donuts are made from scratch, using as many local ingredients as possible. The (not-so) secret ingredient: fresh Maine potatoes. yes, you read that correctly! Adding mashed potatoes gives the donuts a delicious moist texture that makes them just melt in your mouth. In addition to plenty of fresh Maine potatoes, they include the highest quality dark cocoa powder and 60% dark chocolate chips in all chocolate donuts and glazes, and color their glazes with only fruit juices or vegetable dyes, no fake colors. And while they typically sell out, if for some reason they do have leftovers at the end of the day they are donated to organizations such as the Preble Street Resource Center because they believe in giving back to the community. I loved the triple berry and the maple!

Portland Hunt & Alpine Club: Cocktails are a must here! Any cocktail menu that begins with these words below is a winner with me!

A Toast :IF YOU’RE GOING TO LIE, LIE TO SAVE A FRIEND. IF YOU’RE GOING TO CHEAT, CHEAT DEATH. IF YOU’RE GOING TO STEAL, STEAL A PRETTY GIRL’S HEART. AND IF YOU’RE GOING TO DRINK, DRINK WITH ME.

They even categorize their spirits based on certain emotions you might be feeling. I was feeling adventurous so I went with The Green Eyes which consists of gin, chartreuse, lime, and egg white. Lin chose a drink from The Wildcard menu! Alongside their beverages, they serve Scandinavian-esque snacks like shrimp sandwiches, deviled eggs, Swedish meatballs, salmon soup, and a smörgåsbord platter. They also have popcorn and champagne!!! Oui, please.

Bonobo Wood Fire Pizza: At bonobo wood fire pizza their goal is to support Maine businesses as well as make the best pizzas with the best ingredients. They buy from local farms from which they receive their top notch ingredients, such as tomatoes, chicken, goat cheese, and pork. We loved the spinach and leek pizza!! And it was a great place to go with Quin, Lin’s grandson who is a year and a half years old.

Austin Street Brewery: Austin Street Brewery started with Jake's home brewing hobby quickly moving from a casual day off activity to an outright obsession.  The name "Austin Street Home Brewery" started out as way to identify the brews coming out of Jake's garage on Austin St. in Westbrook, Maine.  After years of drinking Jakes home brewed beers and seeing the progression from good, drinkable beer to some of the best beer he's ever tasted, Will convinced Jake that it was time to share his beer with more people.  It was decided that the name would remain, sans the word "home" and thus "Austin Street Brewery" was born. They are currently brewing on a 10bbl system at 1 Industrial Way, the building that has paved the way for a few other breweries including Rising Tide and Maine Beer Co. Their beer can be found on draft all around southern Maine!

Urban Farm Fermentory: Urban Farm Fermentory® is a fermented beverage producer and community engagement hub! It is here that they craft authentic kombucha, cider, beer, mead and jun using local and foraged ingredients! This place was one of my absolute favorites of the whole trip. I just love that they focus on seasonally available ingredients and you can get a sample flight, pour, or growler fill! The tasting room features 24 taps that change daily which you can find on their website!

Corner Room Kitchen And Bar: Enjoy house-made pastas, pizzas, antipasti and artisanal breads here. Harding Lee Smith has dedicated his life to bringing quality local ingredients back to the tables of Maine. Known for his affordable, friendly neighborhood restaurants, this former graduate of Portland’s Deering High School spent the better part of 10 years traveling the world to develop the classic creations that keep Mainers coming back for more and the Bolognese was the best I have ever had in my life!

Inkwell: Once the Portland Press Herald’s busy city room, Inkwell echoes the energy and intellect of its former occupants. You can tap into that energy and turn Inkwell into your satellite office with our coffee bar that serves up espresso, cappuccinos, lattes and more, along with delicious pastries, everything you need to get a job done. For happy hour I recommend one of our hand-crafted vintage cocktails or Portland microbrews or one of the small plates. You have to check out their lobby space that features tables emblazoned with Press Herald headlines spanning 150 years. Swoon!

Eventide Oyster Co.: Their lobster roll is served on Chinese steamed buns and you just gotta try it!

Bard Coffee: At Bard their mission to tell the stories of these people, places and coffees in every cup they serve as though they are fulfilling a promise. They carefully source, roast, and prepare their coffees using only the very best practices in order to bring out and share the most wonderful attributes each has to offer. This coffee was sooooo good!!

Other musts are the chowders at Gilberts, Crudo from Central Provisions, anything and everything from Fore Street, the sample menu at Piccolo!

For shopping you should definitely pop into Portland Dry Goods—painstakingly curated shop offering high-quality clothing, shoes and accessories for men and women. They support smaller brands made in the USA as well as England, Portugal, Ireland and Japan with an emphasis on construction and materials, and I want one of everything! Grab some Vintage treasures from Moody Lords too. And The Portland Flea-for-All is rad too!

Check out the views over The Eastern Promenade too! Portland has so much more to offer than just food but I literally just did the food portion ya’ll. I have 4 more pounds on me to prove it too but I have zero regrets! I also came down with a bit of a tiny cold too so I required lots of sleep on this part of the trip so it was nice to have somewhat of a loose agenda.

Enjoy the dreamy pics above from The Pomegranate Hotel too! We had a great experience in a Lark Hotel in Martha’s Vineyard a few years ago so I wanted to stay in another Lark Hotel! When you book stay in the main house though. We stayed in the carriage house and I really regret that choice! If I ever go back to Portland, I will definitely be booking The Press Hotel though. (the location is perfect) It’s just more me-not saying The Pomegranate is not cool, we just all have different tastes so check them both out and see what works for you!

Day 6: Cape Elizabeth: Stay at Inn By The Sea

It was time to leave Portland and travel to Cape Elizabeth, the small peninsula with rocky ocean views and historic landmarks like the famous Portland Head Light. Located about five miles south of Portland on the southern Maine coast, Cape Elizabeth was named in 1604 by Captain John Smith to honor Princess Elizabeth, daughter of King James I and Queen Anne of Denmark. Its craggy shores and unspoiled sandy beaches extend twelve miles into open ocean forming the entrance to spectacular Casco Bay.

In 1828 the first pair of Cape Elizabeth lighthouses were built to mark the entrance to Portland Harbor. Considered among the most important on the coast, the original towers were replaced in 1874 by 67-foot cast-iron towers, which have been painted white since 1902. The Cape Elizabeth area has borne witness to a number of shipwrecks, one of which bestowed the area with the beloved friendly spirit of Lydia Carver, a bride-to-be who perished in an 1807 storm. Her small antique grave lies near the Inn and has captured the romantic imagination of visitors and residents alike.

Annnd I fell head over heels in love with Cape Liz. We were hosted and completely spoiled at The Inn By The Sea!

And I highly recommend you read my full post on my experience at The Inn By The Sea here! Along with more pics and recs for Cape Elizabeth. You are going to love Crescent Beach State Park so much.

Day 7: Kennebunk and KennebunkPORt: Stay at The Grand Hotel

The Grand Hotel in Kennebunkport, Maine, sits prominently on Chase Hill, just steps away from bustling, downtown Kennebunkport. Featuring classic New England architecture and elegantly appointed decor, the hotel offers views of lively Dock Square and Lower Village. It’s the perfect spot to enjoy your coastal Maine vacation. You’ll find exceptional restaurants, diverse art galleries, and charming boutiques all within walking distance of your room. Explore the waterfront by paddling a kayak down the river. Hop onto one of our complimentary cruiser bikes to meander along the back roads of Kennebunkport. Enjoy a scenic tour on a classic schooner, lobster boat or whale watch. Or spend a lazy day soaking up the sun on one of the area’s pristine beaches. ( in the summer of course) But I have some things for you to experience in the fall and am even sharing a promo code for you in my post about my time and Kennebunkport and The Grand Hotel in this post. The photos are so lovely and I can so see why The Bush’s loved it here!!!!!

End your Maine trip with a trip to Bob’s for a fish sandwich and some ice cream from Rococo’s along the coastal roads into Massachusetts.

It was time to experience fall in Boston!

We are so thrilled to have stayed in Boston’s Seaport District by the way and you can read more about our stay here. I have some great hotel recs for you and some fun places to eat and play!!!!!!!!

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