Peru has the Inca Trail, Boston has the Freedom Trail and Maine has...the Pumpkin Trail!
Maine does a lot of things well. Lobster, beaches, whoopie pies, lakes, sensible boots, sugary sweet drinks...the list goes on and on. But, of all the things we do well, it might be autumn that we do the best. Yesterday we told you all about an awesome fall foliage train trip. Today, we're bringing you something so unique, you likely had no idea it even existed in Maine! Before this season is over (and after the fall foliage train trip, of course) take a journey down Maine's Pumpkin Trail!
Maine’s Pumpkin Trail consists of over 50 miles of some of the most wonderful mid-coast coastline. It includes cruises, train rides, a pumpkin boat race, parades and lots more! The events that are a part of the trail began earlier in September, but we've collected some things that are upcoming!
1. Lighthouse Legends and Lore Cruise - September 30th
This is event is perfect for those with a love of Maine's coastal history. Guided by the "mysterious Lady in the Red Cloak," passengers on this trip will explore seven lighthouses. Among them are: Doubling Point Light, Hendrick's Head Light, Seguin Island Light, Ram Island Light and The Cuckolds. The trip even includes a land-visit to Burnt Island which means exploring the keeper's house and the Burnt Island Light tower.
This wonderful fall celebration is one of the best small mid-coast events of its type. It's great for people who aren't into the huge fairs, but want to get a bit more into that Maine autumn spirit. There will be crafts, live music, barnyard animals, a working blacksmith and other traditional artists and barrel train rides. Click here for more information.
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3. First Friday at the Farnsworth Museum in Camden - October 7th
This month's event will be a celebration for the opening of "The Art of Disaster." This special fall-themed event will include live music, fun treats, interactive photo displays and lots of "pumpkin disasters." We're not entirely sure what that means, but you should click here for more information.
4. Damariscotta Pumpkin Festival and Regatta in Damariscotta - Oct 1 to Oct 10
Of all the things that make us proud of Maine, this could just be number one! On Columbus Day Weekend, head to Damariscotta for the best celebration of pumpkins you've ever seen. Events include the annual Official "Giant Pumpkin Parade," The Pumpkinboat Regatta and The Giant Pumpkin Drop. Yes, folks, this is real. And you'd be crazy to miss it!
5. Pumpkin Fest Baking Contest in Damariscotta - October 8th, 10am
The pumpkin festival is so great that individual events get their own special place on the Maine Pumpkin Trail. This one is definitely the most delicious. The event is open to anyone who wants to try their hand at becoming the best pumpkin-dessert creator in Maine. Participants can make anything they'd like but must include fresh, frozen, or canned pumpkin. Drop off your dessert 10am and 11am. Winners are announced at 1:15pm. The best part? You can taste all the good stuff! Click here for more information.
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6. Pumpkinfest Parade in Damariscotta - October 8th
The pumpkin festivities are just getting started. Enjoy one of the biggest events of the weekend by lining up to see all the fun pumpkin related costumes and some of the largest actual pumpkins you've ever laid eyes on. The parade begins at 2pm. Click here for more information.
7. Pumpkinfest Regatta in Damariscotta - October 9th
And, finally, our absoulute favorite individual event - the regatta! Head to the Damariscotta Harbor, the Lincoln Theater (where you can watch via live-feed) or tune into LCTV local Channel 7 to take in this hilarious event. Competitors in two categories - paddleboat and powerboat - will compete to be named champ. Click here for more information.
8. The Giant Pumpkin Drop in Damariscotta - October 10th
This event is one of the most unique on the trail. Spectators can watch Atlantic Giant Pumpkins being dropped from an 180’ crane onto things such as an old local police cruiser to cars stacked on top of one another! The remnants of the pumpkins is gathered to become pig feed at a local farm, and the cars (which are already junked) are recycled as scrap metal. We only wish this was televised for all the world to see! Click here /a> for more information.
9. Bath Cemetery Tour of Famed Captains and Shipbuilders in Bath - October 12th, 22nd and 29th
Those with a love of all things spooky should make this a must-see. Head to the museum where you'll take a trolley to one of Bath’s oldest cemeteries, Oak Grove Cemetery. The cemetery boasts the most varied collections of memorial art in the town and includes many local, historic maritime families. You'll hear the histories of the shipbuilders in the area and learn all about the symbolism of the ornately done memorials. Click here for more information.
10. The Fall Family Festival at Farnsworth Art Museum - October 15th
This event is a wonderful one for families. Head to the museum sculpture garden for pumpkin carving, face painting, crafts, and live music. Then, watch the parade march down Main Street. Or, even better, participate in it by wearing costumes and masks. The day will conclude with a beautiful pumpkin lighting in the sculpture garden at sunset. Click here for more information.
Doesn't this sound like the perfect way to celebrate fall?
As the leaves stop falling from the trees and the chill becomes just a bit more biting, it’s clear that winter is well on its way here in Vacationland. And, that can only mean it’s time to set off on a winter wonderland adventure! If we’re lucky, the landscape will transform into a calm blanket of snow, bringing various fun activities to enjoy across the state. The season invites locals and visitors to explore the great outdoors by enjoying things like skiing, tubing, fat biking, cross-country skiing, dog sledding, snowshoeing, snowmobiling, ice fishing, and hiking on snow-covered trails. The beauty of Maine creates an incredible backdrop for just about any activity and there are so many things to do in Maine in winter.
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In addition to participating in outdoor activities, I love simply enjoying the way my fellow-Mainers celebrate the season. Light displays, local events and festivals, and some of the most charming Christmas towns can be found across all 16 counties.
Whether you love the adrenaline rush of winter sports or the tranquility of a snowy stroll, there's no shortage of fun to be had. This is certainly a destination that calls to those seeking both adventure and relaxation.
Holiday Events In Maine
Every season is great for exploring the state, but when winter arrives things start to feel a little bit more special. And, there’s no shortage of fun things to do in Maine in winter. From taking in the splendor of local holiday lights to sharing in the community joy of lighting the town tree, there are plenty of ways to have fun. Gather your friends and family and head out to enjoy the many ways that a Maine winter can fill your heart with joy.
1. Gardens Aglow at Coastal Maine Botanical Gardens
Family (2 adults/2 children): $48, Member Adult: $15, Member Child: $8
One of the most beloved events of the year is also one of the most magical. For years the Coastal Maine Botanical Gardens have been inviting guests to experience a display of lights unlike any other. During Gardens Aglow more than 750,000 LED lights are placed throughout 14 acres of the central gardens. With special themed areas, immersive trails, and their famous trolls, this is one of the best events in the region for kids. As one of the most fun family things to do in Maine in winter, be sure to get your tickets early.
Popularity: Busy on weekends, but the lights stay up well into the new year so consider checking them out in January or February for less congestion.
Price: Free
Many of the light displays you’ll see during the holiday season involve tickets and some level of planning. We love that the lights in Portland only require…a visit to this beautiful city! Stroll down Exchange Street, Commercial Street, and other areas in the Old Port area to take in the beauty of one of the most unique light displays in New England. The lights are truly more like an art installation, which makes sense considering they’re created through a collaboration between Portland Downtown and artist Pandora LaCasse. After exploring the Old Port, consider driving around town to see the trees adorned in lights at Deering Oaks and other outlying areas.
There are tree lightings throughout the state, but if you’re coming from away you might find Portland to be most convenient. If that’s the case you certainly can’t go wrong by attending the annual tree lighting in Monument Square. One of the best free things to do in Maine in winter, locals and visitors converge on the square to kick off the season just after Thanksgiving. The tree will be illuminated on November 24, 2023. Be sure to wear mittens and come with a sense of wonder.
There’s nothing quite like the lighting of Nubble Lighthouse in Maine. One of the most quintessential Maine events, the lighting of Nubble might be the most joyous time of the year. This year’s lighting takes place on Saturday, November 25, 2023. Best of all, the lights will remain sparkly and bright until mid-February, 2024. This is one of the most quintessential things to do in Maine in winter.
Christmas Towns In Maine
If ever there was a state made for the magic of Christmas, it’s Maine! Strip away the lights and the snow-covered landscape already feels like a wonderland. But, add a dose of sparkle and some holiday cheer and it’s as if we’ve been transported to one of those Christmas villages you place on your mantel. Here are a few Maine Christmas towns that feel extra-special this holiday season. Plan a long weekend filled with the lights of Main Street, ice skating, and other family-friendly activities for a holiday to remember.
Of all the Christmas towns in the state, this year we believe Lewiston deserves a little extra attention. Those who come from away will want to continue driving past places like Kittery, Portland and Freeport until they reach the city, which might not be on the radar of those looking for quintessential holiday towns in Maine. However, the sparkle here is no less bright than it has been every other year. In fact, this year it might just sparkle more. Make your way to the annual Holiday on the Plaza event at Dufresne Plaza on December 2, 2023 from noon to 5:30 p.m. for ice skating on the ice rink, reindeer, photos with Santa, hot chocolate, horse sleigh and wagon rides along with lots of other fun activities. Be sure to stick around for the tree and Menorah lighting at 5:17 p.m. This year let’s show Lewiston just how much love they have from the east coast to the west coast.
The first weekend in December kicks off the holiday season here in Camden with the annual “Christmas by the Sea” celebration. Santa shows up in a lobster boat ready to bring cheer to Camden as well as the surrounding towns of Lincolnville and Rockport. While there are Christmas-related events taking place throughout the season, we love simply walking around town and taking in the lights lining the downtown streets.
Kennebunkport’s Christmas Prelude might just be the most well-known holiday event in southern Maine. With 20 days of holiday events, fun, and cheer there’s a reason why this period of time is one of the most popular times to visit the small town. Enjoy a parade, the tree lighting and a holiday market among lots of other festivities. Or, if you simply want to visit you’ll find a town filled with beauty and sparkle.
With the help of L. L. Bean, the annual Northern Lights Celebration is one of the most beloved in New England. Taking place on-site at the store’s campus, enjoy a visit with Santa and his reindeer, as well as lots of other events that are perfect for both kids and adults. The town of Freeport takes things a bit further with their annual Sparkle Celebration. This 10-day festival begins on December 1, 2023 and runs through December 10, 2023. Visitors can enjoy a parade of lights, along with a variety of other festive fun.
The small town of Gardiner may not be on the radar of those traveling from away, but it’s certainly one of the most lively Christmas towns in the state. Starting with the annual tree lighting on December 1, 2023 followed by the Gardiner Parade of Lights the very next day, the holidays here are as sparkly as anywhere else in the state.
Outdoor Activities
Year-round, Mainers love to get outside. From hiking to biking and everything in between, this state was made for outdoor enthusiasts. But, wintertime can commonly be overlooked as a great time to enjoy the fresh air. This winter season, consider carving out some time to enjoy a new activity outside. Entry for some state parks and trails is discounted, making outdoor fun one of the best cheap things to do in Maine in winter.
Popularity: Popular on Weekends and school vacation weeks
Price: 2023 - 2024 season pricing is TBD, but will be posted on the Sugarloaf Outdoor Center website when available.
You can make your way to the Carrabassett Valley for a variety of fun outdoor activities, but one of the best one-stop-shops is a visit to the Sugarloaf Outdoor Center located at one of the most popular ski resorts in the region. When you want a break from skiing, consider enjoying some time on the NHL-sized rink. Rentals are available for both kids and adults. The rink typically opes in mid-December and remains open for fun until approximately mid-March. If you’re a hockey lover you’ll want to visit on Thursday night hockey night when sticks and pucks are allowed. During the season, the rink is open daily 9 a.m. to 5 p.m., weather permitting and from 9 a.m. to 7 p.m. during vacation weeks. Kids and adults can enjoy Saturday Family Night Ice Skating from 5 p.m to 7 p.m.
Price: Season passes for downhill skiing range from $180 to $265 depending on age. The mountain also offers passes for just Nordic skiing as well as combo passes for both.
While most people are familiar with places like Sugarloaf, Sunday River, and Camden Snow Bowl, many don’t realize that there are lots of great other options. We love the small, but mighty Titcomb Mountain which is located in Farmington. The 750-foot slope offers 16 alpine trails for all levels, including beginner all the way to expert. There’s also a terrain park for skiers and riders. This ski area is the perfect Maine spot.
Popularity: Popular on weekends and during school vacation weeks.
Price: $34 per person for those 48″ and taller or get a combo ticket for $50 per one child (40″ to 47″) and 1 adult.
There’s nothing more exhilarating than the rush of snow tubing and some of the best can be done in Windham at Seacoast Adventure. Each year they create multiple lanes for tubing and they even have an express lift to the top. That means you don’t need to trudge back up every single time you enjoy a ride. Choose from a single tube or a combo ticket which provides a tube for an adult and a child at a discounted rate. Each session lasts two hours, perfect for plenty of rides!
13. Guided Trail Horse Ride at Carousel Horse Farm
Price: $80 to $125 per session depending on the ride. Visit the Carousel Horse Farm website for updated information.
For a truly unique experience in Maine, head to the Carousel Horse Farm in Casco for a guided trail ride. The farm also offers private rides, as well as rides catered specifically for beginners. Enjoy your time exploring the miles of trails in the region while also learning about the proper care for your horse friend. Rides are especially beautiful in the winter, though you can visit year-round.
Winter Getaways
The only thing better than calling Maine home is having the opportunity to visit. It’s considerably easier to enjoy fun winter activities when you can wake up bright and early and enjoy the day from start to finish. Plan a long weekend, an entire week, or make it a remote-work dream by staying for all the winter months! Whichever you choose, we recommend a stay at any of these unique vacation rentals. Each one is perfect for making a cup of hot cocoa and cozying up with your favorite L.L. Bean slippers.
Price: Varies depending on season, but averages $600 per night.
This ski chalet in Bethel is perfect for those who enjoy skiing. Located about 12 minutes from Sunday River Ski Resort, it’s easy to spend the day on the slopes before returning home for a dip in the hot tub. We love the idea of cooking a meal in the beautiful kitchen, but getting to downtown Bethel for a meal only takes five minutes. There are three floors of living space, and lots of cozy places to hide away with a good book. The point of a getaway can be any mix of relaxation and adventure and this cabin offers both.
Price: Varies depending on season, but averages $475 per night.
Sleep among the trees in this cabin on stilts that feels like a truly unique treehouse experience. The tiny home is one of two on the property and was built to be an eco-retreat. The luxury, carbon-free homes are perfect for taking in the beauty of the Maine forest while also staying conscious of the impact we all have on the environment. The home sleeps four people in two bedrooms and has one bathroom. A stay here is one of the most romantic things to do in Maine in winter.
Price: Varies depending on season, but averages $300 per night.
Located on the banks of the Penobscot River, this waterfront getaway is absolutely fantastic for a quiet getaway either alone or with family and friends. The cottage sleeps up to four people in one-bedroom and other spaces and has one-and-a-half bathrooms. Enjoy your time on the deck looking out over the water or adventure off to nearby places like Mount Desert Island, Acadia National Park and Mid-Coast Maine which are all only 45 minutes away. And, when you’re done exploring you can head back for a relaxing dip in the hot tub. Enjoy Maine on your terms with a stay at this fantastic spot on the water.
Winters in Maine can feel longer than they do in other states. That's why it's imperative that we find as many fun things to do in Maine in winter to keep us busy until the glimmers of spring appear. Have you enjoyed any of the Maine winter activities on this list? If so we'd love to hear your tips and tricks for how to make a visit fantastic. And, if you think we left anything off, please let us know in the comments.
Of course, one of the most important things to keep in mind when enjoying winter in Maine is the cold. As you plan your seasonal fun be sure to check out our ultimate winter packing list to be sure you stay warm and prepared.
Every season in Maine is fantastic, but winter is especially magical. From incredible cold-weather hikes to restaurants that are extra cozy when the temperatures dip, we think Vacationland might just be the best place to be after autumn. There are quite a few reasons to love winter here, but one of the highest on my list is Christmas. And, best of all, each year there are several events taking place throughout the state to help celebrate. From simply enjoying get-togethers with friends and family to taking part in special events hosted by local Maine towns, there are seemingly endless ways to get into the holiday spirit. We encourage you to explore all of them, but a Freeport Maine Christmas might just be our favorite.
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There's a reason Mainers look forward to the Northern Lights event in Freeport every year! It's one of the most magical Christmas events in the state. It typically begins in mid-November and runs through the end of December. That's five beautiful weeks of holiday cheer while celebrating Christmas in Maine.
The fun kicks off at opening night on Friday, November 17, 4-8 p.m. with a tree lighting ceremony at 6:45 p.m. The tree is located just outside the L.L. Bean Flagship Store.
Children and adults alike gathered together to partake in a bit of holiday magic.
Visitors can also enjoy "Holidays Around the World" where visitors are invited to scan codes to learn more about how holidays are celebrated all over the world.
Each day of the week offers another fun activity to enjoy. On Mondays be sure to bring your pet for a photo op with Santa. From Fridays to Sundays, you can visit with Santa and his reindeer in the Holiday Activity Barn. The other days of the week also offer fun events including crafts and even a curling demonstration.
From December 1st through 10th, Visit Freeport hosts the annual Sparkle Celebration which kicks off with a Parade of Lights down Main Street. Freeport is one of the best Christmas towns in Maine, so you'll definitely want to check this out.
If it gets chilly be sure to visit the Warming benches. It offers a place to meet with friends and enjoy a cozy respite from the cold. We were surprised just how warm these benches were offering a great place to sit and still enjoy the lights without having to retreat inside.
Every couple of years L.L. Bean switches things up a bit, in years past they have had a massive singing Christmas tree, a cozy igloo, and an ice rink. This year they will be adding curling to the list of revolving attractions and allow guests to partake in a unique sport they may have never tried before.
Those who love the whimsical parts of the holidays will appreciate the model train village inside the L.L. Bean store. It's set in a quintessential New England town allowing for even more imagination.
There are events taking place throughout the entirety of this beautiful event, but whatever you do be sure to visit Santa and his reindeer! They sit right outside and love little visitors.
There's so much more to experience during the Northern Lights festival, so you might want to visit a few times leading up to Christmas. But if you only have time for one weekend, be sure to make it there for the kick-off and lighting! It's an experience you won't forget.
Check out just how magical this place is by watching this Adventuring in the Moment video. We hope it inspires you to get outside and venture over to this enchanting attraction.
The Northern Lights Celebration takes place at the L.L. Bean Flagship store in Freeport from November 17th through December 31st, 2023. You can learn more about all the ways you can enjoy your time for those magical five weeks by visiting the Northern Lights Celebration website. You can also follow L.L. Bean on Facebook to keep up with the schedule of events or to simply start planning your visit.
After enjoying time in one of the best Christmas towns in Maine, be sure to make your way to Boothbay for Gardens Aglow at the Coastal Maine Botanical Gardens. It's a great way to get into the holiday spirit while being awed by over 650,000 lights. But, be sure to bundle up in something warm. This walk is beautiful, but can certainly get chilly if it's cold outside.
