People book months ahead for the big weekends. Here are the annual festivals, the biggest draws around the Brainerd Lakes, and the weekly community nights near the house.
In calendar order. Dates shift slightly from year to year, but the big weekends fill up early.
A 25-year winter tradition, set for February 4–6, 2027. Pond hockey, sledding, bonfires, a city-wide scavenger hunt, SoupFest, and family activities around town. A good reason to book a winter weekend.
One of the biggest events in the Brainerd Lakes area and a 50+ year tradition. The 1.5-mile parade starts in Crosslake Town Square, with parties, a 5K, a medallion hunt, and green-clad crowds all weekend. Book early if you want to be here for it.
The start of Minnesota’s walleye season is a big weekend on the chain, which hosted the Governor’s Fishing Opener in 2025. A natural weekend for a group fishing trip.
Unofficial start of summer, with multiple activities around town. A good weekend to book if you want the lake before the full summer rush.
A free festival at Crosslake Town Square and on the lake, with a Lake Day and a Loon Fair. It ran for the third year in June 2026 and organizers say it returns in 2027.
Fireworks over the lake, a boat parade, and the usual summer energy. One of the busiest weekends on the Whitefish Chain — book early if you want to be on the water for it.
Usually the second weekend of August. The annual races at Moonlite Bay use boats made of cardboard and glue only, and crowds line the docks and the road to watch. The same weekend in 2026 also brought the 41st annual Crosslake Art Show, the Camp Knutson quilt auction, and the fire department pig roast and car show. Call Moonlite Bay at (218) 692-3575 for this year’s race date and times.
Last big summer weekend, with multiple activities around town. Another weekend that books early.
The classic Up North fall festival. Chili cook-off across town, outdoor arts & crafts fair, Lost Chili Pepper hunt, Cider & Candlelight Tour, street dance, and fall color. Usually the last full weekend of September. A great reason to book a fall stay.
Crosslake’s newest festival, first held October 16–17, 2026. Free entry to the main tent and village on County Road 66, with live music, dachshund races, a costume contest, a stein-holding challenge, family games, and stops at local bars and restaurants across town. Check crosslakeoktoberfest.com for next year’s dates.
Holiday at the Dam at the Crosslake Recreation Area and Whoville Nights in Town Square, both free, make a festive reason for a family holiday stay.
A long-running local favorite at the corner of County Roads 3 and 103, 9 a.m. to 3 p.m.
Worth the drive, and a good reason to base a big group at the lake.
The 37th annual charity ice fishing contest on Gull Lake, about 35 minutes from Crosslake, draws thousands of anglers.
The 55th annual winter festival in downtown Nisswa, about 20 minutes away.
A 60-year summer tradition for kids in downtown Nisswa.
A four-day country music festival at Brainerd International Raceway, with 30+ bands on five stages.
Pequot Lakes’ long-running summer festival, with beans cooked in the ground, plus an arts and crafts fair.
The 45th annual national drag racing event at Brainerd International Raceway, and one of the area’s biggest summer weekends.
An annual shuttle tour of stops around Gull Lake, in its 15th year in 2026.
The 45th annual holiday festival in Nisswa in 2026, free to attend.
Crosslake Fifty Lakes American Legion
35112 Co Rd 3, Crosslake
Tickets around 1 p.m., bingo 1:30–4 p.m. Lunch and full bar available.
14 Lakes Pub & Brewery
36846 County Rd 66, Crosslake
Tickets at 2 p.m., raffle at 2:30 p.m.
Crosslake Fifty Lakes American Legion
35112 Co Rd 3, Crosslake
Usually starts around 6:30 p.m.
Jenkins VFW Post 3839
3341 Veterans St, Jenkins (about 15–20 minutes north)
Friday starting at 5 p.m.
Saturday & Sunday starting at 4 p.m.
Known as one of the area’s largest and most popular meat raffles. Meat from Emily Meats.
Fifty Lakes Bar & Bottle Shop
Nearby in Fifty Lakes
Tickets around 4 p.m., draw at 5:30, bingo at 6 p.m.
For festivals, live music, craft fairs, and other one-time events:
Times and details can change. Call ahead or check the venue’s Facebook page if you’re making a special trip.
The house is on Little Pine Lake, about four miles from downtown Crosslake.
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