This Maine Beach Town Hosts A Halloween Festival With A Dog Costume Parade And High Heel Race

Grown adults race through a seaside fishing cove in high heels at least 2 inches tall. Costumes are encouraged.

Prizes go to the fastest dasher, the highest heel, and the most outrageous outfit.

That alone would be enough for me. But the same weekend also brings a beach parade of dogs dressed in Halloween costumes, complete with judging and awards.

I love that idea. A sandy Maine beach in October, filled with pups dressed as pumpkins, pirates, and who knows what else, sounds like the best kind of chaos.

There’s also a beach plum pursuit, a classic car show, and trick-or-treating for the kids. I have so many questions, mostly about how anyone sprints in stilettos.

Which event would you sign up for first?

A Whole Town Turns Into A Fall Costume Party

OgunquitFest is the fall festival that takes over Ogunquit, Maine, every October. The Ogunquit Chamber of Commerce organizes it, and 2026 marks the 23rd annual celebration.

Mark your calendar for October 23-25, 2026. The festival usually lands on the second weekend after Indigenous Peoples’ Day weekend.

What makes it so fun is how spread out it feels. Events pop up across downtown Ogunquit, Perkins Cove, Main Beach, and other spots around town.

That means you’re not stuck in one crowded field all day. You can wander from a beach parade to a craft fair to a cove full of costumed runners.

The schedule runs from Friday night through Sunday afternoon. Each day brings its own highlights, so plan ahead if you have a favorite event.

Families will find plenty for kids, from trick-or-treating to a special children’s race. Dog owners get their own spotlight too, which feels very fair.

Comfortable shoes are smart for most of the weekend. Save the fancy heels for one very specific Sunday event, unless you enjoy living dangerously.

Honestly, it’s hard to think of a cheerier way to say goodbye to beach season. Ogunquit just does it with extra sparkle.

Good Luck Keeping A Straight Face At Dogtoberfest

Costumed dogs on a sandy beach might be the most charming sight of the whole season. The Dogtoberfest costume parade brings exactly that to Main Beach during OgunquitFest.

It usually happens on Saturday. Pet owners register at the Main Beach entrance, then show off their pups in creative Halloween outfits.

Costume judging and awards take place 2:15 p.m. So if your dog has been practicing its best runway strut, this is its moment.

Main Beach is a gorgeous setting for this kind of silliness. Ogunquit Beach is a long, sandy peninsula with grassy dunes between the Atlantic Ocean and the Ogunquit River.

Planning a costume? Think about comfort first, since happy dogs make the best parade stars.

A simple cape or hat often works better than a full outfit.

Bring water and a few treats for your four-legged contestant. Beach air can make anyone thirsty, especially a dog dressed as a lobster.

No dog? No problem at all.

Watching the parade is free entertainment, and you’ll likely leave with a camera roll full of tiny superheroes and fuzzy pumpkins.

I’m all for any event where the dogs get trophies.

Lace Up Your Highest Heels For A Sprint Through Perkins Cove

Running is hard enough in sneakers. At the High Heel Dash, participants race through Perkins Cove wearing heels at least 2 inches high.

The dash takes place on Sunday afternoon of OgunquitFest. Costumes are encouraged, which turns the race into a dazzling, wobbly parade.

Prizes go to the fastest dasher and to the highest heel that finishes the course. There’s also an award for the most outrageous outfit, so creativity counts as much as speed.

The best part is the cause behind it. The High Heel Dash benefits the Frannie Peabody Center, so every wobbly step supports a good mission.

There is an entry fee for adults and a lower one for kids 12 and under. The road into and out of Perkins Cove closes to traffic during the dash.

That closure matters if you’re driving. Plan to arrive early or park elsewhere and walk in.

Thinking about signing up? Practice walking in your heels before race day, then work up to a light jog.

Your ankles will thank you.

Spectators get a front-row seat to pure fun. Cheering is free, and nobody judges you for laughing.

Kids Get Their Own Race, Minus The Wobbly Shoes

Little ones don’t have to sit on the sidelines during the big Sunday dash. A separate kids’ race runs alongside the High Heel Dash, and it skips the heels entirely.

That’s a smart call. Kids get all the fun of racing through Perkins Cove without any tumbles in borrowed shoes.

A special prize goes to the fastest child. So if you have a speedy runner at home, this might be their big chance to shine.

Costumes add to the excitement here too. A tiny superhero racing toward the finish line is basically guaranteed to make the crowd cheer.

Kids 12 and under pay a smaller entry fee than adults. The money still supports the Frannie Peabody Center, which makes it a nice lesson in giving back.

For the best experience, pick a costume that’s easy to move in. Long capes and floppy masks can turn a sprint into a stumble pretty quickly.

Talk to your kids about the race ahead of time. Knowing what to expect helps nervous runners feel brave.

Then, after the finish line, let them watch the grown-ups wobble by in heels. That part might be their favorite memory.

Candy Hunting Starts Before Halloween Even Arrives

Why wait until October 31 for candy? OgunquitFest gives kids an early head start with trick-or-treating on Friday night and Saturday morning.

The candy trail winds through downtown Ogunquit and Perkins Cove. That gives families two charming areas to explore in costume.

Having both a night and a morning option is really handy. Younger kids who fade early can enjoy daylight treats instead.

Perkins Cove brings a bonus: it’s a scenic spot by the water. Bags filling with candy while boats sit nearby feels very Maine.

Pack layers, since October on the coast can turn chilly. A warm sweater under a costume keeps kids happy longer.

Comfortable shoes are a must, too. There’s plenty of walking between stops, and nobody wants a meltdown halfway through.

Bring a sturdy bag or bucket for the haul. Flimsy bags and full pockets rarely end well.

Here’s a nice family plan for Saturday. Do morning trick-or-treating, then head to Main Beach for the dog parade at 2 p.m.

That’s a lot of joy packed into a few hours. Your kids may sleep very well that night.

Shiny Classic Cars Take Over The Beach On Saturday

Chrome and sand make a surprisingly great pairing. On Saturday, the Classic Car Show rolls into Main Beach as part of OgunquitFest.

That puts it in the same spot as the Dogtoberfest parade. So you can admire costumed pups and polished bumpers in a single trip.

Car shows are fun even if you don’t know a carburetor from a cupcake. Bright paint colors and old-school designs are easy for anyone to enjoy.

Kids often love picking a favorite. Turn it into a game by voting for the coolest, shiniest, or most unusual car.

Remember car show manners while you browse. Look with your eyes, not your hands, since owners spend countless hours keeping those finishes spotless.

Got questions? Many car owners enjoy talking about their rides, so a friendly hello can lead to fun stories.

Main Beach is also near the Autumn Bazaar, which sets up vendors in the Main Beach parking lot. That makes it easy to shop between car sightings.

I can’t imagine a better Saturday combo. Classic cars, costumed dogs, and an ocean view all within strolling distance is hard to beat.

Shop Dozens Of Makers While Live Music Plays

Handmade treasures fill two spots all weekend long. The Artisan Craft Fair at OgunquitFest features around 50 to 60 or more vendors.

You’ll find it at the Dunaway Center, 23 School Street, Ogunquit, Maine. It also spreads to the Dorothea Jacobs Grant Common at 47 Cottage Street.

Food trucks and live music join the fair, too. So you can shop, snack, and tap your toes all in one stop.

This is a great place to start holiday shopping early. Handmade gifts feel more personal than anything grabbed off a store shelf.

Bring a tote bag to carry your finds. Some vendors may prefer certain payment types, so having a little cash on hand is a smart backup.

Hungry? Grab something from the food trucks and find a spot to listen to the music.

Since the fair runs all weekend, there’s no need to rush. Visit once to browse, then return later for that item you keep thinking about.

That’s my kind of thinking. A fair that sticks around for days gives everyone room to shop without stress.

Whoopie Pies, Pumpkins, And Gourds Make Things Delightfully Silly

Maine’s official state treat is the whoopie pie, so of course there’s an eating contest. The Whoopie Pie Eating Contest takes place at the Old Village School Playground on Cottage Street.

Fluffy cake and creamy filling make for messy competition. Spectators get plenty of laughs, and contestants get frosting everywhere.

Not big on speed eating? OgunquitFest has gentler games, too.

The Painted Pumpkin Pursuit gives visitors a festive activity to enjoy around town. It’s a fun way to explore while spotting colorful seasonal decorations.

Then there’s Guess the Gourds, a guessing game with a prize. Trust your instincts, or just pick a lucky number and hope for the best.

These smaller events help fill the gaps between the big headliners. They’re perfect for families who want to stay busy without spending much.

Thinking of entering the whoopie pie contest? Arrive with an appetite and maybe a few napkins tucked in your pocket.

Also, wear clothes you don’t mind getting smeared. Frosting stains are basically a badge of honor here, but your favorite sweater might disagree.

Pack Pet Food And Leave Room For Ocean Views

Kindness is part of the festival lineup, too. Visitors are encouraged to bring non-perishable food or pet food to donate.

Donations go to the York County Shelter or the Animal Welfare Society. It’s a fitting touch for a weekend that celebrates dogs so warmly.

Toss a few cans or a bag of kibble in your trunk before you leave home. It takes almost no effort and helps people and animals in need.

Once you’ve done your good deed, save time for Ogunquit itself. The town sits on the southern coast of Maine and has plenty to explore.

Marginal Way is a cliff walk with coastal views, benches, and a lighthouse. A fall stroll there pairs nicely with festival fun.

Art lovers can visit the Ogunquit Museum of American Art. It’s known for waterside sculptures and works by Maine-related artists.

Check museum hours before you go, since fall schedules can change. Planning ahead keeps your weekend smooth.

Between costumed dogs, racing heels, and seaside walks, Ogunquit makes October feel special. Just remember to save your fastest shoes for the dash.