As summer wanes into fall in Southeast Alaska, there’s renewed energy surrounding all of the holiday celebrations in Sitka! From Alaska Day and Halloween to ringing in New Years Day, there’s something fun in store for everyone. Take a look at the lineup of our favorite seasonal events that intertwine timeless traditions and simple pleasures in a small town.


With crisp weather and crunching leaves underfoot, the peak of fall graces Sitka in a beautiful combination of fall colors contrasted by green foliage and the striking blues and grays of the Pacific Ocean.

October 18th – Alaska Day

Alaska has a long and fascinating history, having been inhabited by indigenous people for thousands of years before the arrival of Russian explorers in the 18th century. In 1867, after negotiations between Russia and the US, Alaska was officially transferred to the US for the sum of $7.2 million. On October 18, 1867, the American flag was raised for the first time in Sitka, marking the end of the Russian Empire’s presence in Alaska and the beginning of a new era for the state. Alaska Day has been celebrated ever since, with parades, reenactments, and other events that showcase the unique heritage and character of Alaska and its people.

October 31st – Halloween

One of the best parts of any Halloween celebration is the costumes, and Downtown Trick or Treating in Sitka is no exception. Participating businesses go all out in creating themed decorations and costumes, making it a visual feast for attendees. Children (and adults!) are encouraged to dress up as well, and they often go out of their way to coordinate with the businesses they visit. It’s a great excuse to let your creativity run wild and truly embrace the Halloween spirit.


Be welcomed by cool, misty mornings in Sitka that make for some of the most serene cold-water dips or bike rides to be had throughout the month in November. The possibility of rain means cozy days spent perusing shops, dining out, or for the adventurous, time spent hunting, beachcombing or storm watching.

November 3rd -6th – Sitka Whalefest

Whalefest, Sitka Alaska is an annual event that celebrates the rich marine life of Southeast Alaska, particularly the majestic whales. This festival is a celebration of the immense beauty and diversity of marine life, as well as highlighting the importance of marine conservation. Attendees of this festival get to witness firsthand the breathtaking spectacle of whale sightings, enjoy educational and entertaining activities.


Bright and twinkling lights, beautiful handmade garlands, and holiday cheer can be felt all throughout December in Sitka. Spirits are bright all season long, from photos with Santa to Light Up Lincoln Street.

December 2nd – Light Up Lincoln Street

It’s that time of the year again when the air is crisp and the streets are adorned with lights, decorations, and festive cheer. Christmas is just around the corner and Sitka, Alaska is all set to welcome it with open arms. One of the most significant events that mark the start of the holiday season in Sitka is the annual Light Up Lincoln Street. It’s a spectacular evening when the entire community gathers together to light up the town and enjoy the magic of the festive season.

Families, friend groups, couples, and everyone in between head to the Sitka, Alaska during the holiday season for some rest and recuperation or uninterrupted time with loved ones. Holiday availability tends to book out well in advance of the holidays, if you’re considering a trip to Sitka, take a look now to make sure you get the best accommodations for you and your crew.

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