Travel Guide: Fall Day in Kennebunkport and Kennebunk, Maine

I’m finally editing my photos from our weekend in Maine and ended up with so many that I had to figure out a way to split them into two posts: enter an itinerary for a fall day in Kennebunkport, Maine. This was an easy way to take 15 photos out of what could have been a 40-photo post on our entire long weekend, plus, this is an optional add-on to a Portland itinerary. It just made sense to split it out. So, let’s get into it (and, also, let’s take a moment to rejoice for the return of travel guides!). 

Our trip to Maine was one that almost didn’t happen. We initially had the trip booked for June…then it became the beginning of October…then, the last week of October, we had a realization: travel was going to become iffy, fast, and, if we wanted to try to get out of DC one last time, we needed to do it ASAP. So, we rebooked our trip and did the required quarantine, test, quarantine routine necessary to visit Maine. We were able to spend 3 days in the Portland area experiencing a New England fall (and experiencing what it’s like to dine outside in 25 degrees…). 

One quick warning: because we visited in late fall, most of the seasonal spots had closed! So, we didn’t get to visit some of the most lauded lobster rolls shops and the like. 

A Fall Day in Kennebunkport

Spending a fall day in Kennebunkport actually wasn’t on our initial itinerary. So, the interesting thing about the way we travel is that, beyond where we’re staying, I don’t love to do a ton of planning (okay, let me rephrase that, I am usually too busy to do a ton of planning). It drives Adam, who loves to have restaurant reservations in place weeks in advance, crazy, but it leaves us room for a spur-of-the-moment day trips like this one to Kennebunkport.

So, how’d we end up here? Well, our weekend in Portland happened to be rainy and cold…we felt a little bit trapped staying in the city, like maybe there wasn’t quite enough to do outdoors given the temperature. We started looking up nearby day trips and 30 minutes to Kennebunkport couldn’t be beat. I mean, if we’re going to be walking around in the chilly rain, might as well do it in a charming waterfront town, right?

 

 

Arrival in Kennebunkport

Once we started driving from Portland to Kennebunkport, I was like THIS is what I expected from Maine. Totally adorable, with restored 19th century homes lining established streets with fall leaves peeping around every corner. It doesn’t get more quaint than this.

As we parked, I wondered if I’d been transported into a Gilmore Girls episode (I mean, I’ve never actually seen it, but I’m pretty sure this is the vibe). I grabbed a cardamom caramel latte at Fiafia, a cute little cafe that we came across just a block from where we parked.

Side note: traveling off season is always wonderful but even more so when you’re hoping to avoid people.

 

Walk Around Kennebunkport Into Kennebunk

Since spending a fall day in Kennebunkport wasn’t on our original itinerary, we didn’t have much of a plan upon arrival. Fortunately for us, there’s a clear main street to walk down so we strolled through town, across the water, and down to the outskirts of Kennebunk. I believe there is an actual little downtown of Kennebunk, but we only saw a few shops and restaurants that are right after you cross the water from Kennebunkport (There’s one fellow blogger who I know will be able to correct me if I’m wrong here! Looking at you, Annaliese!)  

We stopped in Live Cafe when we saw a sign that they carried Holy Donuts, the famous Portland potato donut that we’d been dying to try (we even happened to hit it when they were selling the previous day’s donuts for half off, so we may have gone a bit crazy). And, with donuts and coffee in hand, we decided we needed to find somewhere to sit down for a few chilly moments to enjoy our snacks…

 

Stroll Around the Franciscan Monastery

Wandering around in search of a place to sit led us to the grounds of the Franciscan Monastery and, while I’m not 100% sure whether they actually own the park around them, that seemed to be the case, with multiple chapels dotting the landscape around the monastery. We took to the walking trails and found a clearing with a small deck by the water, perfect for sitting with a cup of coffee and appreciating the gray fall morning on the water. All the photos you’ll see below are from that park.

 

Take a Walk Through Charming New England Neighborhoods

As we walked back into town, I couldn’t get enough of the delightfully quintessential New England homes and the winding streets. I’m sure the fall leaves (which we weren’t even sure we’d see in late October!) didn’t hurt the scene. It’s seriously enough to keep you occupied for an entire afternoon just to stroll around, imagining what these homes might look like inside, and trying to keep yourself from Zillow’ing the price of any house with a “For Sale” sign.

 

Stop for a Drink at Batson River Brewing and Distilling

As we walked back into town, we stopped in Batson River Brewing and Distilling solely because the branding and ambiance was perfection. Seriously, that hunting dog logo is all of the New England fall feels I want (to clarify: just want the dog motif, not an actual dog). There was a vintage black pickup truck overflowing with pumpkins parked out front and smoke billowing from multiple fire pits. Could I ask for any more?

I can’t recall exactly what we got but Adam did order a beer while I opted for a cocktail. Both were great and you just can’t beat sipping a drink while looking out over the river.

We were on a one cocktail limit since we had to drive back to Portland and had planned a brewery stop on the way but, if we’d had more time, we would have liked to check out Maine Mead Works across the street.

 

Do a Little Shopping Around Dock Square

If you’re in the mood to shop, there is a vibrant shopping area in downtown Kennebunkport around the Dock Square area. Surrounded by the river and a quaint over-the-water shops, this is somewhere you can appreciate even if you’re not looking to walk away with any great finds.

We stopped in Dock Square Clothiers, where Adam found a shirt (they have both men’s and women’s clothing), and Kate Nelligan Design, a bright and colorful store perfect for waterfront decor. Funny enough, she even had one product, a candle in a can, that referenced the Rappahannock River in Virginia, where my parents have their river cottage.

 

Head Back to Portland

Kennebunkport is an easy day trip from Portland and, while I wish we’d had just a few more hours to explore (or just a little less rain), it provided a welcome change of scenery and, seriously, the most charming seaside ambiance. It’s everything I pictured New England to be.

And, on the way out of town, we made a quick driving stop by Walker’s Point, because Adam wanted to see what the Bush compound looks like. Just as we were driving by, the rain and wind started to pick up, and, in the photo below, you can see the power of the ocean that resides next to this quaint town.