Tip Included
How To Spend 48 Hours & $480 On A Weekend Trip To Kennebunkport, Maine

How To Spend 48 Hours & $480 On A Weekend Trip To Kennebunkport, Maine

Psst, Taylor Swift filmed one of her music videos here.

Ariela Basson/Elite Daily; Getty Images

As a born-and-raised Jersey Girl* (*author’s note: I am nonbinary) who lived in Boston for five years before making my way to New York City, I’ve always wanted to cross “travel to every state on the East Coast” off my bucket list. Up until last week, I only had one state left to hit: Maine.

Known for its beautiful shorelines and serene landscapes, Vacationland — as Maine is often referred to — is an idyllic destination for a weekend getaway. And about 30 miles south of Portland, celebs have already caught wind of Kennebunkport as a desirable spot.

Taylor Swift filmed her “Mine” music video in nearby Kennebunk, slightly more inland from Kennebunkport, and even McDreamy himself, Patrick Dempsey, returned to his home state of Maine to purchase a home in town a few years ago.

As far as weekend accommodations go, there are more than a few hotels and charming bed & breakfasts in Kennebunkport, and dozens of Airbnb options as well. Since Bloomingdale’s graciously offered to host my girlfriend and I at Hidden Pond resort, about a ten-minute drive from the center of town, I opted to stay a couple of nights at one of its adorable little mountain bungalows.

Abby Lebet
Abby Lebet

Upon walking into the cabin, we were greeted with a room full of screened windows and chaise lounge chairs, perfect for basking in the fresh Maine air; I affectionately dubbed this the “breeze room” during my stay.

It was the perfect, luxurious, glamping experience — emphasis on the ‘glam’ part.

Inside, soaring ceilings and a cozy fireplace made the space feel so inviting, and I was immediately giddy with excitement over the lavish outdoor shower. It was the perfect, luxurious, glamping experience — emphasis on the “glam” part — and with the help of Camp Bloomingdale’s summer camp essentials, I was equipped for every excursion on my itinerary.

While Kennebunkport tends to run on the pricier side compared to more rural weekend hotspots, it was a little easier to mitigate expenses having traveled with my partner. Also, some hotels and resorts offer an array of activities either for free or for a discounted rate, so that may also be worth looking into to minimize costs.

Ahead, find everything worth seeing in Kennebunkport with my 48-hour itinerary for $480, tip included.


3:00 p.m.: Arrive at Portland, Maine Jetport

As an NYC resident without access to a car, flying up to Maine ended up being the best option for me, and the hour-long flight from JFK Airport to the Portland Jetport went by in a blink. By the time we were cleared to use our laptops on the plane, we were just about ready to land.

From there, it was a half-hour drive south to my resort, and there were plenty of options available via ride-share apps like Uber and Lyft for under $50.

If you’re already located in the Northeast, driving may be your best option (it’s about a six-hour trip from NYC). For New England-based visitors, Amtrak also runs the Downeaster line from Maine to Massachusetts and passes through nearby Wells, ME, which is only about 20-25 minutes from Kennebunkport.

Rideshare from airport to Hidden Pond: ~$42

6:00 p.m.: Dine at Earth restaurant

Once I got settled in my cabin, I changed into nicer clothes and took a short walk over to the esteemed Earth restaurant, located inside the resort.

Admittedly, I knew this would likely be my big food splurge of the weekend and had high expectations going in — one of my friends who dined there before has absolutely raved about it, and I’m happy to report I, too, was delightfully impressed by my own experience there.

Abby Lebet

The restaurant itself had a simultaneously rustic and modern interior, and the cuisine was remarkably delicious. While many restaurants call themselves “farm-to-table,” the food at Earth tasted particularly fresh, as if it could’ve been harvested seconds before landing on my plate.

I selected a glass of Albariño wine to complement my nourishment for the evening, then proceeded to dine on a four-course dinner of roasted carrots, barley risotto, scallops in a pea puree topped with caviar, and delectable sassafras doughnuts for dessert.

Scallops with caviar in pea puree at Earth restaurant

Abby Lebet

Though dining at Earth can get pretty costly, I was beyond satisfied with my nosh. I went a little over-budget, but even a three-course meal ($110) would still include plenty of food to feel satisfied. 100% worth the splurge.

Dinner at Earth: ~$110

9:00 p.m.: Snack on s’mores by the campfire

Abby Lebet

After I finally finished digesting dinner, I hung outside by the campfire and snacked on a tasty, post-dessert s’more. Hidden Pond hosts the campfire every night with supplies included for resort guests.

If that’s not an option where you’re staying, I’d still recommend bringing a s’mores kit to your accommodations and making them over the stove (or in the microwave, if you’re feeling fancy) to get a similar vibe.

10:00 p.m.: Doze off after a good dose of fresh air

Following long day of travel and great food, I went back to my bungalow and curled up under a blanket in my aforementioned “breeze room” to take in some cool, fresh air before calling it a night.

DAY 1 TOTAL: $152


8:00 a.m.: Wake up with breakfast pastries

I slept super well in the bungalow, but I’m naturally a morning person, so even with all of the curtains and blinds closed, I was awake by the time the sun fully rose (around 6:30-7 a.m.).

Thankfully, my resort delivered complimentary coffee and pastries for breakfast every morning, so I enjoyed a delicious, fresh-baked slice of blueberry loaf and cup of coffee in bed.

10:00 a.m.: Practice watercolor painting

I constantly feel inspired being out in nature, and the views in Maine are so tranquil, I wanted to spend the first few hours of my day practicing mindfulness and indulging my creative energy. So, I signed up for a watercolor painting class.

Once everyone arrived and got settled, our instructor did a demonstration to show us some painting techniques we could use to achieve different petal and leaf shapes, which was helpful to get started. I chose to paint a pretty orange flower with some leaves coming off the stalk. It’s certainly not a perfect image, but, hey I’m only a novice painter.

Abby Lebet

My finished product!


All of the materials, including the paper and paints, were provided by Hidden Pond, and all we had to do was select one of the plants on display to model our illustration on.

The resort typically offers free classes on Mondays and Wednesdays to guests, but River Tree Arts Center in Kennebunk also hosts watercolor and acrylic painting workshops, including supplies, throughout the summer for $40-42.

Watercolor painting: $40

11:30 a.m.: Immerse yourself in nature on a walk

Since I was already feeling so inspired from my watercolor class, I ventured out on a nature walk. I’ve been getting a lot of #forestbathing content on my For You page and wanted to understand what the hype was about. I concluded it was essentially a mindfulness walk, but I still appreciated the Maine landscape.

If you’re interested in a guided walk, some tour guides tend to charge less per person in large groups, or there are plenty of great free parks and grounds to check out like The Smith Preserve or St. Anthony’s Franciscan Monastery for some pretty views of the Kennebunk River.

2:00 p.m.: Take a mixology class

By this point, I decided I could use a drink, so I attended a mixology class where I learned how to make a couple of drinks on the Earth restaurant menu. I’d never tried my hand at bartending before, but it was easy to learn and fun to sip along the way.

Abby Lebet

The class is only offered on Saturdays, open to the public, and the $50 cost (pre-tax and tip) includes all of the supplies you’ll need. You can reserve your space online in advance.

Mixology class: $65 (tip included!)

3:30 p.m.: Bike to Goose Rocks Beach

There are a handful of bike rental spots around Kennebunkport, so after mixology, my partner and I decided to grab a couple of bikes and took a breezy, 15-minute ride over to Goose Rocks Beach.

Contrary to its name, the beach is mostly sandy with plenty of space to lay out in the sun, but with ocean temps of around 50°F in mid-May, it wasn’t quite warm enough to go swimming yet.

Nonetheless, the views were so picturesque. Scenic mansions dot the coastline atop a rock wall (presumably to protect from any storm surges), and the water was fairly calm, the tides gently lapping at the shore. It was easy to imagine how peaceful it would be to lay out in the sun and go for a quick dip in the water to cool off.

Coastal mansions at Goose Rocks Beach

Abby Lebet

If Goose Rocks Beach is too far, Colony Beach is also free and open to the public, and is easier to access from many of the popular hotels in downtown Kennebunkport. Mother’s Beach and Gooch’s Beach are also free, but if you’re driving, definitely reserve a beach pass for your car. And if you’re renting a bike, keep an eye on the time — most of those shops close down at 5 p.m.

Regardless of which beach you choose, I’d definitely recommend bringing some sunscreen, even if it’s cloudy outside (speaking from experience because I got a little burned that day).

Bike rental: $29

6:00 p.m.: Enjoy an outdoor shower

By the end of the bike ride home, I had worked up a sweat, so I enjoyed a relaxing and restorative outdoor shower back at our bungalow.

I always used to take outdoor showers when I’d vacation at the Jersey Shore with my family as a kid, so this made me feel super nostalgic. I loved how private and secluded it felt, and it was so serene to look up and see only trees all around me.

The view from the outdoor shower

Abby Lebet

If you don’t have access to an outdoor shower, light a scented candle and consider a luxurious bubble bath or a steamy everything shower (plus a glass of wine if you’re feeling it) to cool off and indulge in some self-care.

7:00 p.m.: Attend a lobster bake

Since I was in Maine, I *had* to try the seafood — most notably, lobster — and it seemed like a traditional lobster bake would be the perfect place.

Not only was there plenty of lobster, but I had a hearty cup of clam chowder, an ear of corn, and some garlic bread to round it out. Plus, strawberry shortcake and blueberry crumble for dessert.

Abby Lebet

Bloomingdale’s and Hidden Pond hosted the bake for our trip, but you can also book one at other locations like White Barn Inn for $95 per person.

Since dinner went for a few hours (and I was already pretty beat from the bike ride and afternoon at the beach), I was pretty tired by the end, and decided to ship off to bed early for the night.

Dinner: $95

DAY 2 TOTAL: $229


8:00 a.m.: Wake up and eat breakfast pastries

This morning, I was greeted with a couple of buttery croissants, which paired really well with jam and some orange juice. Checkout is usually around 10-11 a.m., so after breakfast, I prepped my suitcase to head back to the airport.

10:00 a.m.: Go shopping around town & grab a bite to eat

I would definitely recommend taking a few hours to peruse the shops in downtown Kennebunkport and the main commercial areas. It’s only a short, 10-15-minute drive into the center of town from where I stayed, and fairly walkable once you’re there.

DenisTangneyJr/E+/Getty Images

There are lots of cute stores to find souvenirs and tchotchkes, plus restaurants, distilleries, art galleries, and so much more. A local Kennebunkport expert recommended La La Luna and Daytrip Society for boutique clothing and lifestyle shops.

For a bite to eat, Mornings in Paris has some unique French bites and sips, like a flowering cherry latte and sweet or savory crepes.

Rideshare to shopping area: ~$17

Food & shopping budget: $40

3:00 p.m.: Travel back to Portland Jetport

My biggest recommendation coming out of this trip, especially if you want to enjoy more nature and the landscape of Maine in the Kennebunks, it would be a lot easier to get around with a car rather than taking rideshares everywhere. But for just a couple of days, if you’re staying generally on the beaten path, it’s still totally doable. One last half-hour Uber to the airport, and my 48 hours in Kennebunkport had come to an end.

Rideshare back to the airport: ~$42

DAY 3 TOTAL: $99

Total Cost: $480

If I had unlimited time (and funds), I would’ve loved to stay longer in Kennebunkport and explore more of the surrounding areas. Also, for all my Swifties, you can visit the filming locations for Taylor Swift’s “Mine” music video, like Cape Porpoise and Christ Church, and maybe head over to Alisson’s Restaurant for a bite after.

I definitely see myself coming back to Kennebunkport with my partner (and maybe our our dog next time too).