Head to Maine for a three-day getaway filled with holiday memories!

Christmas in Maine Day 1: Portland

1. Explore Old Port - Downtown Portland 

Downtown Portland is incredibly family-friendly and easy to explore. Whether your kids are walking or riding in a stroller, the area is compact, has wide sidewalks, and is simple to navigate with plenty of places to pop into. The cobblestone streets and waterfront views make it extra charming as you take in more than 150 shops and 60 restaurants. Shops and restaurants are fully decked out for the holidays, especially along Commercial, Exchange, Pearl, and Fore Streets.Be prepared to shop for yourself, the kids, or for gifts, Portland’s shopping scene is seriously underrated. From niche boutiques to well-known brands, the variety is amazing. Grab Portland-famous donuts from Holy Donut or Eighty 8 Donuts as your family wander (plus kids need to refuel). Treehouse Toys was my kid’s favorite stop, offering a huge selection of toys, books, and gift ideas. And yes, you’ll spot plenty of lobster-themed merchandise and food everywhere you go!

2. Find a Lobster Trap Tree or Two

No holiday visit to Maine is complete without seeing a lobster trap tree. The two main ones are located right in downtown Portland, making them easy to spot as you explore. The Portland Regency Hotel and Spa features a buoy-covered lobster trap tree in its turnaround for everyone to enjoy, and Porthole Pub on Custom Wharf Road has an impressive one displayed on its deck.

3. Batson River Brewing & Distilling 

Arguably, the best holiday-decorated restaurant in Portland and an absolute must for lunch or dinner. Batson River Brewing & Distilling is truly stunning with every inch  filled with festive spirit. It’s family-friendly, and kids will be happy just by taking in the decor. It's a wow place. The holiday drinks are fun, the food is delicious, and there are plenty of options even for picky eaters. The lodge area even has arcade games for built-in entertainment. Reservations are tough to snag, so keep checking or try for a walk-in right when they open. Arrive about 10 minutes early and expect a line to build. it’s absolutely worth it. Walk from downtown in about 20–25 minutes, or drive and take advantage of the convenient adjacent parking lot.

The kids will love all the family-friendly activities on a Christmas trip to Maine for the 2025 holidays!

4. Go Ice Skating at Thompson's Point 

Who doesn't love Ice skating? It makes for a perfect family adventure. Head over to Thompson’s Point for an outdoor rink offering public skating sessions with skate rentals available on-site. Don't worry, there are plenty of skating aids for all levels. Additionally, the rink offers two heated seating areas and a small concession stand for quick snacks. The rink is spacious and has a unique view. You can even watch planes take off from Portland International Airport right across the way. Check their website for public skating times since they vary per day. 

Depending on your family's schedule and pubic skating, Thompson’s Point sits in a prime family-friendly area. The Children’s Museum & Theatre of Maine is right across from the rink—a three-story indoor attraction perfect for families with younger kids. The second floor was a major hit with my little ones, filled with pretend play spaces and a craft room. On Sundays, the parking lot buzzes with the beloved Makers Market. A great spot to browse local small businesses and pick up unique gifts.

5. Christmas Ship Parade

End the day with something unique and festive lights! For 15 nights, around 80 privately owned ships illuminate the shoreline. A tradition since 1954, the Christmas Ship Parade sails along the Willamette and Columbia Rivers. Be sure to check their website for the schedule so you know the best spots to stand and watch with your family.

Free port Maine, home to L.L. Bean, has some amazing holiday sights for a Christmas getaway!

Christmas in Maine Day 2: Freeport and Boothbay

6. Freeport Outlets

Another coastal town that’s great for shopping and snacking with the whole family is Freeport. The Freeport Outlets have fun local spots like Palmer and Company, Wicked Whoopies, and Two Sisters in Maine, along with big names like J.Crew Factory, Vineyard Vines Outlet, and Patagonia Outlet. It’s the perfect place to stroll, browse, and pick up gifts. Best of all, the outlets sit right next to L.L. Bean’s flagship store.

7. L.L. Bean and The Northern Lights 

With their headquarters based in Freeport, L.L.Bean is a local favorite and a must vist. The multiple category-specific stores, L.L. Bean feel like a shopping campus! Stock up on their signature tote bags, cozy sweaters, flannel shirts, and of course, the iconic boots. Don't forget to take a photo for the giant boot!

During the holiday season, L.L.Bean hosts Northern Lights, a completely free event in Discovery Park. Check their website for activities by day and times. I would recommend shopping before and plan on walking the Northern Lights starting around 3 o'clock. Enjoy photo ops with Santa and Mrs. Claus, fire pits with heated seating, hot chocolate stands, and the Winter Spectacular. All activities take place outdoors, so be sure to bundle up for the winter weather.

Santa and Mrs. Claus will be stopping by L.L. Bean in Freeport, Maine for Christmas 2025!

8. Gardens Aglow at Coastal Maine's Botanical Garden 

Take a quick hour drive and end the night with a whimsical light festival at Coastal Maine Botanical Gardens. Their one-mile outdoor path, Gardens Aglow, is such a fun experience for families of all ages. The incredible New England light show transforms the gardens into a magical walk with glowing scenes inspired by Maine’s forests, beaches, and meadows. Food and drinks (including alcohol) are available at the Snack Shack. Reservations are required through their website and tend to book up quickly, so plan ahead.

Christmas in Maine Day 3: Kennebunkport and York

9. Walk and Shop the Town of Kennebunkport

Did you know Kennebunkport was named the #2 Christmas Town in America by HGTV?! Walking through the center of town truly feels like stepping onto a Hallmark Christmas movie set. This coastal town is adorable on its own, but once the garland and holiday decorations go up on every storefront, it becomes pure magic. Dock Square and Ocean Ave are the main spots for shopping. There’s truly something for everyone to love it here: Stadium Gallery for sports fans, Daytrip Jr. and Next Generation Children’s Clothing for little ones to explore toys, and the beloved Lobstore: Gifts with Coastal Charm for all things lobster. Take a family photo in front of  Kennebunkport’s Christmas tree in the center of town. The large tree is beautifully decorated with buoys and lobsters. Getting hungry while you walk? 

Kennebunkport is famous for its Christmas Prelude. It's an 11-day celebration packed with festive events that bring the community and holiday spirit to life. You’ll find everything from Santa arriving on a lobster boat, caroling throughout town, fireworks, and unique parades (hat parade and the pooch parade). It’s easy to see why this town ranks among the top Christmas destinations. There’s even special Prelude merchandise and accessories available. If you’re visiting between December 4–14, 2025, be sure to check the official website for the full schedule of events, times, and locations.

The quaint streets of Kennebunkport await a family holiday getaway for Christams 2025. 

10. Seashore Trolley Museum 

Take in the scenic views of Kennebunkport with a charming trolley ride! Seashore Trolley Museum is extra special because it’s part of the world’s first and largest electric railway museum. Since it is off season, the trolley's schedule is  Thursdays-Saturdays from 10AM-4PM until May. And if you’re lucky, you might even get the chance to try operating a trolley car yourself - such a fun surprise for both kids and adults! Check their website to book a reservation. 

11. Nubble Lighthouse

No trip to Maine is complete without seeing a lighthouse! Just a few miles away in York, Nubble Lighthouse is one of the most photographed lighthouses in the world and even appears on the Maine state quarter. During the holidays, it transforms into a beautifully lit landmark that glows against the night sky. Who doesn't love a coastal life view?

Where to Eat During Christmas and the Holidays in Maine

12. Portland

Besides, Batson River which is a must, Portland's restaurant is unreal which is amazing, but can be overwhelming. Among the many places in the Old Port, DiMilio's, on the Water—a floating restaurant with a vast selection of Down East favorites— will delight families looking for a (very) low-key water excursion. Becky's Diner is a local fave for hearty breakfasts. And Otto's Pizza has multiple locations and some delectable, creative pies.

13. Freeport, Yarmouth, Boothby

My family and I absolutely loved stopping at Royal River Grill House in Yarmouth for lunch on our way to Freeport. The heated porch is cozy and charming, straight out of a coastal Pinterest board. The kids’ menu is one of the best I’ve seen, with healthy options and plenty of coloring and activities to keep little ones entertained while waiting for their food. Don’t miss the festive holiday drinks, and be sure to try the Bloody Mary- it’s served in a Grey Goose bottle, which makes it feel extra special!

Other family places near the Freeport area include Buck's Naked BBQ and Studio Bar, Gather, and Maine Beer Company. 

14. Kennebunkport and York 

Kennebunkport has a Christmas decorated restaurant inside the Kennebunkport Inn, The Tinsel Bar. You need to make reservations for dinner. There are plenty of great options like Alisson's Restaurant, The Boathouse Restaurant, and Federal Jack's. Batson River Brewing & Distillery is also a fully decorated Christmas-themed spot, just like the one in Portland. My kids insisted on eating here again, because they loved the food and wanted another look at the festive interior.

Maine Hotels for a Holiday Stay

15. Hyatt Place Portland Downtown-Old Port Square - Portland

The Hyatt Place Portland Downtown is a great spot for families to stay. It’s right in the heart of the Old Port, so you can easily walk to tons of restaurants, shops, and all the fun exploring Portland has to offer. From babies in strollers to tweens, the location is an underrated gem for families who don’t want the hassle of driving and finding parking. The hotel offers a Breakfast Bar for an easy start to the morning and has plenty of room options with pullout couches for larger families.

16. The Press Hotel - Portland

The Press Hotel is a great choice for families who want a stylish, unique stay right in the heart of Portland. Located at the corner of Exchange and Congress Streets in the Old Port, it offers easy walking access to restaurants, shops, and activities. The hotel has 110 beautifully designed rooms including a Penthouse Suite with rooftop access and incredible city views which is plus larger room options that work well for families.

17. Cliff House Maine - Cape Neddick

If you’re looking for a charming Maine hotel right on the coast, Cliff House is the perfect pick. It’s more than just a hotel, it really feels like a full resort. The views are absolutely breathtaking, and you’ll definitely snap plenty of family photos on the cliffs. Cliff House also has two on-site restaurants, an indoor pool, and a relaxed atmosphere that makes it easy for families to spend time outside their rooms. Trust me you’ll be raving about this place to friends and likely already planning your summer return before you even check out.

18. The Kennebunkport Inn - Kennebunkport

Kennebunkport Inn is a great choice for families, located in the heart of downtown Dock Square. Each morning, a complimentary to-go breakfast gets the family out the door quickly, and the on-site restaurant plus nearby kid-friendly eateries make mealtime simple. The inn offers cozy, character-filled rooms with spa-style bathrooms and fireplaces in some rooms. The private parking is worth it with the town parking being limited with crowds. With its mix of comfort, charm, and a prime location, Kennebunkport Inn is the perfect low-stress base for exploring the town.

All photos courtesy of the author