To Travel the world is to travel within oneself. For all the adrenaline junkies out there are cool adventure events in Oconomowoc like hiking in the forests, camping in mountains, hanging by the cliffs and a lot more. An adrenaline rush is sure to have when one is out there on adventure. Whether it’s swimming, river rafting, rappelling , riding with motorcycle club or cycling with friends or just a weekend getaway near Oconomowoc, we have got you covered.
Find your adventure and trips near Oconomowoc.
## Trips & Adventures Events in Oconomowoc - **Event Name**: Trail Run, Walk & Roll - **Description**: The 5K, 10K & half marathon courses are set on Zachariah's Acres 100 acres consisting of tree-lined paths, wild flowers, prairie grass, ponds, wild life, crops, and more. The family walk/roll loop is 1 mile of gentle hills and scenic views. Jogging s - **Interested Audience**: - Count: 105 - **Date**: Sat Oct 10 2026 at 09:00 am (-05:00) - **Event URL**: https://allevents.in/oconomowoc/trail-run-walk-and-roll/200029789039352 - **Venue**: N74 W35911 Servants’ Way, Oconomowoc, WI, United States, Wisconsin 53066 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy9kMzU1OGI3YjhjZDdiYjEwNzFlMzk2YjU2NTg3ODlmOTJlMzQ4Njc1NTBkODkwZmZjYzZiNjlkNWI0ZmU0Njg1LXJpbWctdzEyMDAtaDY3NS1kY2Y4ZjhmOC1nbWlyP3Y9MTc4ODI2NDQ1Mw.avif - **Categories**: trips-adventures, marathons, sports, workshops ## Trending Events in Oconomowoc - **Event Name**: Business Trick or Treat - **Description**: We know how much fun it is to dress up and collect treats. But we also know that staying up late for traditional, after-dark trick-or-treating can be tough (and sometimes a little spooky) for the younger crowd. That’s why we’ve put together a special tri - **Venue**: 173 E Wisconsin Ave, Oconomowoc, WI, United States, Wisconsin 53066 - **Banner**: https://cdn-az.allevents.in/events8/banners/03287cf69933e5a982b5e47765c3dbf5265b0f229ed6e67b453541ee13dd863b-rimg-w1200-h675-dc2878b8-gmir?v=1787263770 - **Event Name**: Oconomowoc Fall - Witches Night Out - **Description**: Oconomowoc Fall Witches Night Out 2026- Join us for a magical evening of shopping, sipping, and spooky season fun! A limited number of swag bags will be available, Swag bag pick-up and a photo backdrop will be located at the front of the Avenue Square Ma - **Venue**: Wisconsin Ave, Oconomowoc, WI 53066, United States - **Banner**: https://cdn-az.allevents.in/events10/banners/c1482aebf125233d146060d2fa14ab63cf3784ee5f173d774f026331564121d4-rimg-w1200-h675-dcf8f8f8-gmir?v=1787216976 - **Event Name**: Pumpkin Run - **Description**: Race #1: Winter Run Series Join us for the 22nd Annual Winter Run Series, Wisconsin’s largest running series! This exciting series event takes you through the heart of Milwaukee and its scenic suburbs, showcasing the city’s charm and beauty. Spanning si - **Venue**: Fowler Park - 438 N Oakwood Ave, Oconomowoc, WI 53066 - **Banner**: https://cdn-az.allevents.in/events2/banners/924b717bff20720d4f97b615132945f69b0c88e86da5166b622d3213fce4525f-rimg-w1200-h400-dcf8a848-gmir?v=1787620055 - **Event Name**: Inflatables in the Outfield - Fall 2026 - **Description**: Inflatables In The Outfield RETURNS OCTOBER 10 & 11 The Ultimate Stadium Playground is back this fall OVER 30 INFLATABLES COVERING THE ENTIRE FIELD! BOUNCE HOUSES • GIANT SLIDES • OBSTACLE COURSES • INTERACTIVE GAMES The Entire Stadium Becomes A Gian - **Venue**: 1011 Blue Ribbon Circle N, Oconomowoc, WI, United States, Wisconsin 53066 - **Banner**: https://cdn-az.allevents.in/events2/banners/4c0da298575315cf3635845d06ca7bc0e7c21fc040c8d7f436838a07272040bc-rimg-w1200-h675-dc2888c8-gmir?v=1788544057 - **Event Name**: Dracula The Ballet - **Description**: Community Partners Event 7PM Friday & Saturday, Oct 9-10 2PM Saturday & Sunday, Oct 10-11, 2026 Darkness rises this fall as Dracula The Ballet returns to the Oconomowoc Arts Center for three thrilling performances. Presented by BrayBallet Co. in - **Venue**: 641 E Forest St, Oconomowoc, WI, United States, Wisconsin 53066 - **Banner**: https://cdn-az.allevents.in/events6/banners/81b4150f123f41cc16731d22bbbebdf9028b9a62e86f2d413bc57531a86ce4cb-rimg-w1200-h628-dc080808-gmir?v=1788332960 - **Event Name**: TRADES5K - **Description**: TRADES5K Run/Walk brings the trades together to connect and support a fellow trades family. Join us for this one-of-a-kind event!About this EventGET READY FOR TRADES5k!Join - **Venue**: N381 Franklin Rd - **Banner**: https://cdn-az.allevents.in/events10/banners/eb8120bbc4d3332726993889439a9a7e565ce94208e8c5e632ad3e3c1ba1719b-rimg-w1200-h600-dca7a9ad-gmir.jpg?v=1782092884 - **Event Name**: 5th Annual Haunted Corn Maze - **Description**: Join us this year for our 5th annual Haunted Corn Maze! The first entrance to the maze at 7pm and last entrance at 10pm! Tickets can be purchased online and are are also available for purchase day of in the farm store. The farm will open both nights - **Venue**: Jelli's Market - **Banner**: https://cdn-az.allevents.in/events7/banners/9a309696b25acc3b91d2b00450498ca76b4cc0fa613c2a8695cab10b5f86d2b9-rimg-w1080-h1350-dc080808-gmir?v=1790853711 - **Event Name**: Fall Pancake Breakfast - **Description**: Join us at Jelli’s on October 11th from 8–11 AM for a fun, family-friendly Farm Breakfast! After our farm-to-table dinners, we wanted to create something the whole family could enjoy..and breakfast felt like the perfect way to do it! Come enjoy a pancak - **Venue**: Jelli's Market - **Banner**: https://cdn-az.allevents.in/events3/banners/63148c9337f7e0dece4d5b89973e527f324d8c4633249e50bb21c7ef4af16d56-rimg-w1200-h1552-dcf8f8f8-gmir?v=1787040418 - **Event Name**: CCLS Annual Dueling Pianos Fundraiser - **Description**: Creative Community Living Services (CCLS) is hosting our annual Dueling Pianos Fundraiser on October 24th in Oconomowoc at Cornerstone Pub & Eatery. Get ready for a night of fun with performers Howl2GO! The night includes good music, hors d’oeuvres - **Venue**: Cornerstone Sports Pub & Eatery - **Banner**: https://cdn2.allevents.in/thumbs/thumb6a847ce77d849.jpg ## Browse Trips & Adventures Events by Date - [Trips & Adventures Events Today in Oconomowoc](https://allevents.in/oconomowoc/trips-adventures--today) - [Trips & Adventures Events This Weekend in Oconomowoc](https://allevents.in/oconomowoc/trips-adventures--this-weekend) - [Trips & Adventures Events in October in Oconomowoc](https://allevents.in/oconomowoc/trips-adventures--october) - [Trips & Adventures Events in November in Oconomowoc](https://allevents.in/oconomowoc/trips-adventures--november) ## FAQs - **Q**: What are the top Trips & Adventures events in Oconomowoc? - **A:** Trail Run, Walk & Roll (Sat Oct 10 2026 at 09:00 am at N74 W35911 Servants’ Way, Oconomowoc, WI, United States, Wisconsin 53066). - **Q**: What Trips & Adventures events are happening in Oconomowoc this weekend October 9–11, 2026? - **A:** Trail Run, Walk & Roll (Sat Oct 10 2026 at 09:00 am at N74 W35911 Servants’ Way, Oconomowoc, WI, United States, Wisconsin 53066). - **Q**: What Trips & Adventures events are happening in Oconomowoc in October 2026? - **A:** Trail Run, Walk & Roll (Sat Oct 10 2026 at 09:00 am at N74 W35911 Servants’ Way, Oconomowoc, WI, United States, Wisconsin 53066). - **Q**: How can I find Trips & Adventures events in Oconomowoc? - **A:** You can discover upcoming Trips & Adventures events in Oconomowoc on AllEvents.in. Browse by date, venue, or price to find events that match your interests. - **Q**: How do I buy tickets for Trips & Adventures events in Oconomowoc? - **A:** You can buy tickets directly through AllEvents.in. Many events offer online booking with options for free, paid, and early-bird tickets. - **Q**: What are the popular venues for Trips & Adventures events in Oconomowoc? - **A:** Some popular venues hosting Trips & Adventures events in Oconomowoc include N74 W35911 Servants’ Way, Oconomowoc, WI, United States, Wisconsin 53066. - **Q**: Who are the top organizers for Trips & Adventures events in Oconomowoc? - **A:** Popular organizers hosting Trips & Adventures events in Oconomowoc include Zachariah's Acres. - **Q**: Are there any online Trips & Adventures events available? - **A:** Yes, many Trips & Adventures events are available online. You can filter for virtual events on AllEvents.in to attend from anywhere. - **Q**: How can I get notified about new Trips & Adventures events in Oconomowoc? - **A:** Follow the Trips & Adventures category on AllEvents.in to get notified when new Trips & Adventures events are listed in Oconomowoc. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/d4/526b9c2f9443799c294c7c3b6e3343/freepik__candid-photography-with-natural-textures-and-highl__27226-1.webp ## Trips & Adventurous Activities from nearby cities - [Trips & Adventurous Activities in Delafield](https://allevents.in/delafield/trips-adventures) - [Trips & Adventurous Activities in Watertown](https://allevents.in/watertown-wi/trips-adventures)