October is bringing all the fall magic to the Lakes Region! 🍁🎃 From vibrant foliage and festive fall markets to seasonal adventures, live entertainment, and family-friendly fun, there’s no shortage of ways to celebrate autumn in New Hampshire. We’ve rounded up some of the best local events to help you get out, explore, and soak up everything we love about this beautiful time of year! 🍂✨
October 13th - October 18th, 2026
🧠🍻 Put Your Trivia Skills to the Test at DOX!
Think you’ve got what it takes to win? Round up your smartest friends and head to Dox on Winnisquam for a night of trivia, delicious food, cold drinks, and a little friendly competition! 🎉💡
Test your knowledge, compete for great prizes and gift cards, and enjoy a fun night out with friends. Don’t forget to check DJ Trivia for clues that could give your team a few extra points! 🏆🍔
📍 Dox on Winnisquam | Tilton, NH
🗓️ Tuesday, October 13
⏰ 7:00–9:00 PM
🏆 Prizes + Gift Cards
🍔 Food + Drinks Available
🎟️ Table Reservations Recommended
Grab your crew, bring your A-game, and see if your team has what it takes to claim the trivia crown! 🧠🏆🍻✨
For More Information ⟶ https://www.lakesregion.org/event/trivia-night-dox-on-winnisquam-tilton-nh-2-2-2-2/2026-10-13/
🕺🎤 Get Ready to Moonwalk Down Memory Lane!
The King of Pop takes center stage at The Colonial Theatre with the Michael Jackson HIStory Show—an electrifying tribute celebrating the music, moves, and unforgettable legacy of one of the world’s most iconic entertainers! ✨🎶
From Thriller and Billie Jean to Smooth Criminal, Beat It, and Bad, experience all your favorite hits brought to life by tribute performer Garth Field, a live band, incredible dancers, authentic costumes, and spectacular stage effects! 🪩🔥
📍 The Colonial Theatre | Laconia, NH
🗓️ Wednesday, October 14
⏰ 7:30 PM
🎟️ Tickets: Approximately $44–$90
🎶 Live Band + Choreographed Dancers
✨ Full-Scale Tribute Production
Whether you’re a lifelong Michael Jackson fan or just love a night of great music and entertainment, this high-energy show will have you singing along from start to finish! 🎤🕺✨
For More Information ⟶ https://www.lakesregion.org/event/michael-jackson-history-show-the-colonial-theatre-laconia-nh/
🍂🪦 Step Back in Time at Castle in the Clouds!
Discover the stories of those who came before us during the Graveyard History Walking Tour at Castle in the Clouds! 🏰🍁
Explore the historic grounds once known as Ossipee Park, where remnants of old cemeteries and cellar holes offer a fascinating glimpse into the past. Along the way, learn about the families who once called this land home, their lives, and the funerary traditions of early New Hampshire residents. 🌲📜
📍 Castle in the Clouds | Moultonborough, NH
🍁 Featured Date: Thursday, October 15
🗓️ Select Dates: October 5–24
⏰ 1:00–3:00 PM
🎟️ $15 per person | Pre-registration required
🥾 Approximately 2-mile guided walking tour
📍 Meet at the picnic pavilions by Shannon Pond
With beautiful fall foliage as your backdrop, this unique experience combines local history, a little mystery, and the natural beauty of the Lakes Region! 🍁🏰✨
Be sure to wear comfortable walking shoes and dress for the weather, as the tour includes inclines and uneven terrain. Registration closes at 10 PM the day before each tour.
For More Information ⟶ https://www.lakesregion.org/event/graveyard-history-walking-tourmondays-saturdays-october-7-october-28-2024-castle-in-the-clouds-moultonborough-nh-2-2/2026-10-15/
🍻🍁 Fall Brews & Lake Views!
Trade summer sunshine for sweater weather and set sail on Lake Winnipesaukee for the Beveridge Brews Cruise aboard the M/S Mount Washington! 🚢🍂
Enjoy an unforgettable evening sampling some of New Hampshire’s best seasonal beers and ciders while cruising past the beautiful fall foliage. From Oktoberfest lagers and spiced ales to fresh autumn releases, there’s something for every craft beverage lover! 🍺🌊
📍 M/S Mount Washington | Wolfeboro Town Docks
🗓️ Friday, October 16
⏰ 5:30–9:00 PM
🎟️ $60 per person | Ages 21+ Only
🍺 Unlimited Samples of Local Fall Brews
🎶 Live Acoustic Music
🍂 Fall Snacks Available for Purchase
🚢 Scenic Lake Winnipesaukee Cruise
Gather your friends, grab your favorite fall sweater, and raise a glass to autumn on the Big Lake! With limited capacity and tickets expected to go quickly, be sure to reserve your spot! 🍁🍻🚢✨
For More Information ⟶ https://www.lakesregion.org/event/beveridge-brews-cruise-m-s-mount-washington-from-wolfeboro-town-docks-wolfeboro-nh/
🎃🛍️ Shop Local with a Spooky Twist!
Get ready for a little shopping, creativity, and Halloween fun at The Village at Paugus Bay October Makers Market! 🍂👻
Explore a wonderful collection of local artists, crafters, and small businesses showcasing handmade treasures, unique gifts, and one-of-a-kind finds. Plus, this market comes with a little extra Halloween magic—costume contests, pumpkin carving, trick-or-treating, and spooky face painting for the whole family! 🎨🎃
📍 The Village at Paugus Bay | 131 Lake St., Gilford, NH
🗓️ Saturday, October 17
⏰ 10:00 AM–3:00 PM
🎟️ FREE Admission
🛍️ Local Artisans + Handmade Goods
👻 Costume Contests for Kids & Adults
🎃 Pumpkin Carving Contest
🍬 Trick-or-Treating Throughout the Village
🎨 Halloween Face Painting
Throw on your favorite costume, bring the kids, and spend a fun fall day supporting local makers while enjoying a little spooky-season excitement! 🍁🧡👻✨
For More Information ⟶ https://www.lakesregion.org/event/the-village-at-paugus-bay-october-makers-market-gilford-nh/
🍁✨ A Little Fall Magic on Squam Lake!
Get ready for a weekend of shopping, creativity, and lakeside charm at Squam Fest: An Enchanted Market! Formerly known as the Vintage Market on Squam Lake, this beloved fall event is back with a fresh twist and even more to explore! 🛍️🍂
Browse an eclectic mix of vintage treasures, handmade jewelry, unique artwork, upcycled clothing, home décor, and locally crafted goods. Enjoy live music, delicious food trucks, seasonal cocktails, and even tarot and intuitive readings—all set against the beautiful backdrop of Squam Lake! 🔮🎶
📍 Cottage Place on Squam Lake | Holderness, NH
🗓️ Saturday, October 17 | 9:00 AM–4:00 PM
🗓️ Sunday, October 18 | 10:00 AM–3:00 PM
🎟️ $5 for the entire weekend | Children 12 & under FREE
🛍️ Vintage Finds + Local Artisans
🔮 Tarot + Intuitive Readings
🎶 Live Music
🍴 Food Trucks + Cocktails
🎁 Purchase tickets online for a chance to win a local gift basket!
Gather your friends, soak up the fall scenery, and spend a little time discovering one-of-a-kind finds while supporting local makers and small businesses! 🍁🧡✨
For More Information ⟶ https://www.lakesregion.org/event/squam-fest-an-enchanted-market-cottage-place-on-squam-lake-holderness-nh/2026-10-17/
There’s no shortage of ways to get out and enjoy the Lakes Region this week. We hope this guide helps you make the most of it while supporting the amazing local businesses and events that make our community so special.
