New England Travel Guide: A Fall Weekend in Portland, Maine

So, this fall weekend in Portland, Maine was originally supposed to be a summer weekend in Maine…but, hey, I’m not going to complain about rescheduling a trip to coincide with the changing leaves in New England! We spent two days exploring the Portland area and, while a warm weather or early fall trip will guarantee that you avoid seasonal closures, I like to think a slightly off season adventure can give you a quieter, more low-key look at the region.

I also wrote a travel guide on a day in Kennebunkport, ME. You can find that here!

A Fall Weekend in Portland, Maine

We went to Portland the very last weekend in October, first weekend in November: Saturday, October 31 through Monday, November 2. As I mentioned in our Kennebunkport post, we went right before we had a feeling things might start to shut down again. But, assuming the world is now headed in the right direction, going this year should hopefully be realistic.

How to Get to Portland and Get Around

We took a Southwest flight out of BWI. Unless you plan on staying downtown throughout your trip (and you could — there’s certainly enough to do!), I would recommend renting a car. You’ll want it to get around the city and to explore the surrounding areas. 

Where to Stay in Portland

We chose to stay at a hotel downtown, the Hyatt Old Port. While I typically like staying places with a bit more character and, on this trip, I perhaps would have even considered staying somewhere slightly remote outside town, we had points. So, big hotel chain it was.

When to Go for a Fall Weekend in Portland

Like I mentioned, going late in fall will be more of an off-season feeling. We were super lucky that, despite leaf predictions, we happened to be there while there were still plenty of vibrant oranges and reds dotting the landscape. Ideally, you’d probably go a bit earlier — late September, early October.

Also, I’m trying something new here so, if you want to read my day-by-day, hour-by-hour itinerary, keep on going. If you’d prefer to just run through a list of recs, click the link below.

Jump to Recommendations by Category!


weekend in portland maine - scarborough lobster - best lobster roll portland


Day One: Fall Weekend in Portland

First Stop: Stop By Scarborough Lobster in Scarborough, ME

Our first stop after leaving the airport was a lobster shack in Scarborough, ME, just a few miles south of Portland, in order to find an authentic Maine lobster roll. My research wasn’t super scientific. It consisted of googling the best lobster rolls in the Portland area, bypassing the ones that looked a bit too trendy or sleek. I was fine with something hyped up — I just wasn’t looking to spend $35 for Instagrammable ambiance.

That search led us to Scarborough Lobster A roadside spot on Route One, Scarborough Lobster had all the fisherman vibes I was looking for. The lobster roll was overflowing with giant chunks of lobster. Super simple, super delicious. It’s a no frills spot that focuses on doing one thing well and they crush it.

Note: we also ordered stuffed clams. They were good enough but I’d probably pass on them and just order more lobster.


weekend in portland maine - scarborough lobster - best lobster roll portland

fall weekend in portland - old port portland


Second Stop: Check Into the Hotel, Grab a Coffee, Explore Downtown

After we were full of mouth-watering, succulent lobster, we drove into town to drop off our luggage and check into our hotel. Like I mentioned, we booked the Hyatt because we had points and Adam has Hyatt status but it worked to our advantage. They upgraded us to a suite on one of the top floors with a balcony overlooking the city and the water. Sure, I love my boutique inns, but I’ll take it. 

Once we were situated, we walked out our hotel and almost immediately came upon a walk up window for Bard Coffee. Never one to turn down a coffee experience, I grabbed a latte to go, and we spent some time strolling around downtown popping into shops. 

I wasn’t particularly in the mood to shop but, if you are looking for some retail therapy, there’s so, so much to explore


fall weekend in portland - old port portland - bard coffee window portland


Third Stop: Sip on a Cocktail (or Mocktail) at Vena’s Fizz House

Our first stop after caffeinating and getting a feel for downtown was Vena’s Fizz House, a craft cocktail bar carrying drinks made from the most intentional and thoughtful ingredients. The inside looked like a moody, intimate space but we braved the cold to sit outdoors.

I wasn’t yet feeling a drink (y’all, I hate day drinking, I can’t help it), but I ordered a mocktail that was incredible. While the specific drink I ordered is no longer on the menu, these combinations should give you a feel for what they carry: Maple syrup, apple cider syrup, lemon, ghost pepper, bitters or coconut crème, blackberry, honey, lime juice, bitters.

Adam, on the other hand, did indulge in a citrus-inspired craft cocktail.

Completely coincidentally, my brother-in-law drew my name for Secret Santa this past year and, knowing I love a good cocktail, he found Vena’s online and got me their Spirit Sipper Infusions. A mix of dried fruits, herbs, bitters, and sugar, you fill the jar with liquor and let it steep. I can’t recommend the Campfire Bourbon enough! Seriously, it’s the scent I want to fill my home with all the time.


fall weekend in portland - old port portland - vena's fizz house

fall weekend in portland - old port portland


Fourth Stop: Austin Street Brewery

At this point, you may be wondering how many stops this day has. Six. Hey, you’ve got to fit in a lot when you’re only in a city for a few days, right?!

Austin Street Brewery’s Fox Street Tasting Room was a quick five minute drive from our hotel downtown but we could have walked there had the sun not been setting quickly — we came dressed for 40 degrees, not 25 degrees with wind chill. 

However, we could stand the outdoor chill while at the brewery. They had their system down pat, with every patron that walked in being directed to a table. And, let me tell you, every Maine brewery was a hit with me because they actually had well-done dark beers. The Six Grain Stout was my choice at Austin Street.


fall weekend in portland - old port portland - austin street brewery portland


Fifth Stop: Woodford Food and Beverage

To be totally honest, I wish we’d just done dinner at Woodford Food and Beverage. We had reservations here for pre-dinner appetizers and cocktails but it was so, so good and their outdoor space was perfection with outdoor heaters at each table and the kindest waiters.

We ordered oysters, the smoked trout mousse, the soup of the day (I believe it was a chowder), and the bourbon old fashioned and I wish we’d had time to dive into the entrees. I even toyed with going back the next day…and, if we’d had another day, we probably would have found ourselves here again.

But, instead, we went on to our dinner reservation…

Sixth Stop: Fore Street

Fore Street came recommended from almost every person we talked to. It’s supposedly one of the best restaurants in town. And the vibe is rustic yet elevated, the type of place that feels woodsy, intimate, and warm despite its high ceilings and industrial accents

So, we wanted to love it. But every single item we tried to order was sold out. I can’t recall what we ended up getting. I know there was foie gras involved — and that was delicious — but, honestly, I can’t remember what else we had because it was our second and third choices. Would I go back? Definitely. The ambiance was fantastic and all the recs can’t be wrong. I just don’t have much to say about our own experience.


fall weekend in portland - woodford food and beverage


Day Two: Fall Weekend in Portland

First Stop: Pick Up Coffee at Tandem Coffee

Day two was our day trip to Kennebunk and Kennebunkport but we kicked things off by swinging by Tandem Coffee on the way out of town. I would have loved to see the interior of this gas station turned laundromat turned coffee shop but the walk up window was also pretty darn cute.

The drive to Kennebunkport is only 30 minutes or so but you’ll be delighted at the views and the charming quaintness of rural Maine. Need more than coffee to fuel up for the drive? Pick up potato donuts at Holy Donut for a sugar rush.


fall weekend in portland - tandem coffee portland

fall weekend in portland - holy donut portland


Stop Three: Lobster Rolls and Beer

Where was Stop Two, you ask? That was Kennebunk and Kennebunkport! Now we’re back in Portland.

One lobster roll isn’t enough while in Maine, so we stopped by the Bite Into Maine food truck, which happens to reside in the parking lot of an industrial park that’s home to several breweries, including Allagash (which was only open for pickup). What a great way to spend an afternoon, right?! You can get your lobster roll three different ways: Maine (mayo, chives), Connecticut (warm with butter), or Picnic (coleslaw, butter, celery salt). Adam got the flight of all three but I’m a purist — though, unfortunately for Portland, a purist of the butter type. Regardless, I’d highly recommend whichever you choose to go with. 

With our bevy of lobster rolls in hand, we walked across the way to Foundation Brew, where, again, I was able to order a Coffee Burnside Brown Ale. Y’all, I’m telling you, Maine treated this dark beer lover right. Definitive Brewing was right next door and we picked up a few beers for the hotel on our way out.


fall weekend in portland - bite into maine food truck allagash - foundation brewing portland


Stop Four: Do a Little Shopping at the L.L. Bean Outlet

Of course, while in Maine, we had to stop by the L.L. Bean Outlet Store. We actually just went to the L.L. Bean mega store at first and were like, so…what’s the big deal? There’s a lot of stuff but the prices are the same as online? But, then, we looked up the outlet. This is there the magic is.

I got this waxed vest, which I’ve worn all winter for half off, and Adam picked up a pair of gumshoe bean boots for a song. It’s 100% worth spending a few hours out here if you happen to be in the Portland area.

Stop Five: Dinner at EVO

Maine meets Mediterranean is the description of Evo, a sleek two-story restaurant that just happened to be right next door to our hotel (seriously, we didn’t plan it…but it worked out conveniently given that it was 30 degrees and raining by that evening). 

It doesn’t appear that their menu is online, which I recall from when I was researching it (just kidding, Adam does all our food research — I just look at the menus), but I can tell you that everything is wonderful. There was a tasting menu option which we planned on doing, however our reservation was too late to allow for the two-hour experience. Instead, we ordered basically everything on the menu. And it was all delicious. So delicious that we brought our leftovers back to DC with us. My mouth is watering just looking at those pillows of pita, that creamy hummus and crunchy falafel, and that spicy tartare.


fall weekend in portland - evo portland


Day Three: Fall Weekend in Portland

Stop One: Coffee at Little Woodfords

Always stop to get a coffee. That’s my number one rule when I’m traveling. And, while I mentioned that Adam does all the restaurant research, I’m the one on the coffee. So, of course, I stumbled upon the adorable Little Woodfords

This darling pink building is only doing coffee to-go during COVID, but I placed an order online ahead of time. Maybe I didn’t understand the system but I did struggle with knowing when my order was ready — and, as a result, waited outside in the snow and wind for about 20 minutes for my maple latte. My latte was scrumptious, however, and I suppose worth the wait.


fall weekend in portland - downtown portland


Stop Two: Watch the Surfers at Higgins Beach

We wanted to make sure we saw the beach, from the beach, so we took a short drive out to Higgins Beach. This was a recommendation from my friend (and wedding photographer!) Lauren, who had gone to Maine during the warmer months.

Honestly, I loved the vibe here so much, even on this gray, blustery day. You have the classic East Coast beach houses but flanked by evergreens and rocky coasts. It’s everything I imagined about New England. If I was to visit Portland during the summer, I might consider staying here rather than in town. 

But, the best reason to go out here: to marvel at the surfers who were out, even on a windy day in freezing rain. 


fall weekend in portland - fall on higgins beach

fall weekend in portland - fall on higgins beach

fall weekend in portland - fall on higgins beach

fall weekend in portland - fall on higgins beach

fall weekend in portland - fall on higgins beach


Stop Four: Drive Up and Down the Coast

I’ll be 100% honest, we didn’t mean to end up at this point in Cape Elizabeth. We were actually looking for the Portland Head Light but stumbled upon this Cape Elizabeth Light instead (fact: there are a lot of lighthouses in Maine). 

And I’m glad we did. We got an up-close view of powerful waves crashing against the rocks, likely even more impressive than normal thanks to the snowstorm that was rolling in. 


fall weekend in portland - cape elizabeth point

fall weekend in portland - cape elizabeth point

fall weekend in portland - cape elizabeth point


Stop Five: Portland Head Light

Finally, we made out way to the Portland Head Light and Fort Williams Park. When you think, “lighthouse”, there’s a decent chance that the Portland Head Light. is what you’re thinking of. It’s the most photographed lighthouse in the world (who knew there was such a title?!). 

The walk up to the lighthouse is impressive and the park itself is massive, with stunning views over the water. This is clearly a vibrant piece of the Portland community, with fields and park space throughout. Had it been a beautiful summer day, we would have brought a picnic and stayed a while. We did stay a while, even in the cold, but spent it walking throughout the park, taking in the fall foliage, and reading historical markers along the way. 

One of the coolest spots on the property is Goddard Mansion, an incredible stone home that’s fallen into ruins. It was still a functioning home just over 100 years ago so it’s crazy that it was allowed to go into a state of disrepair.

Whether you’re spending a fall weekend in Portland, summer, spring, or winter, dress accordingly and definitely include both the Portland Head Light and the park itself in your itinerary.


 portland head light - fort williams park maine

portland head light - fort williams park maine

 portland head light - fort williams park maine


Stop Six: Grab Lunch at Duckfat

After a chilly afternoon at the Portland Head Light, we needed to warm up, so we headed to Duckfat in search of poutine. Turns out, it’s a popular place, but after a quick walk around downtown and seeing similar waits elsewhere, we decided to brave it. 

We waited an hour…in 26 degree temperatures. 

Was it worth it? The poutine was incredible. 100% worth it. Skip the panini. Just get the poutine and all the sauces for a side order of fries. While it wasn’t enough to warm us up, we definitely left with full, happy bellies and headed to the Jetport (fun fact: Portland’s airport is a “jetport” not an airport) for the quick flight back home.


fall in portland - duckfat portland - poutine portland maine

fall in portland - duckfat portland - poutine portland maine


Okay, I’m trying out something new here. When I asked whether people preferred an itinerary or recommendations for travel guides, the answer was split. From my perspective, the itinerary makes sense in terms of chronological photos, but I totally understand why straight recommendation lists make more sense for actual planning. So, I’m doing both!

You just had the run through of my play-by-play itinerary for a fall weekend in Portland, ME and now I’ll recap it all by category. Like this idea? Let me know!

Recommendations by Category | Fall Weekend In Portland

Hotel in Portland

Coffee Shops in Portland

Restaurants in Portland

Places to Grab a Drink in Portland

Activities in Portland

Day Trip From Portland


1 Comment

  1. February 23, 2021 / 11:25 am

    Aside from The Holy Donut, I haven’t been to any of these Portland spots! You’re giving me so many ideas for future trips home. 🙂 So glad the foliage stuck around for you guys too!

    xoxo A

Leave a Reply