To our guests: We are having the time of our lives living in Highwood, IL and everything we picked or chose to do for the wedding was so we could share that with those that we hold dear. Even if we weren't having a wedding this weekend, THIS is what we would be doing (Check out our "Story"). Between Fall rustling through Fort Sheridan, the Great Highwood Pumpkin Fest lighting up the night, and Highwood's famous night life. For us, it's an adventure mixed with a never ending staycation, and we wanted to share that with all of you.

Below are a few of the highlights we thought you might enjoy while visiting, or considering even if you live local.

The Great Highwood Pumpkin Festival, the largest outdoor celebration on the North Shore, returns from October 1–4, 2026. The festivities kick off with a Community Night and Opening Carnival on Thursday, followed by a full weekend of seasonal activities including all-you-can-carve pumpkin stations and the iconic nightly lightings of the massive pumpkin walls.

The festival grounds will feature two stages of live music, carnival rides, and a variety of food and beverage vendors. Attendees can also participate in festive traditions such as costume contests, pumpkin pie eating competitions, and trick-or-treating. Interactive seasonal installations are scattered throughout the event, and leashed dogs are welcome to join in the autumn fun.

https://www.visitlakecounty.org/the-great-highwood-pumpkin-festival-2026-10-01

28 Mile Distilling Co. is a premier North Shore cocktail lounge and live music venue located right in the heart of Highwood. Stepping inside feels like a modern trip back to the roaring 1920s, featuring chic Art Deco decor, soaring ceilings, and exposed brickwork. Guests can enjoy beautifully handcrafted, grain-to-glass cocktails made with their own award-winning bourbon, vodka, tequila, and gin. Between the vibrant Bourbon Lounge performance stage, an intimate tasting room, and the largest rooftop bar area on the North Shore, it is an incredible spot for out-of-town wedding guests to grab a high-end drink and enjoy local nightlife.

https://www.28miledistilling.com/

A favorite past time of patrons of Miramar is to browse the STORE at Ablaze Design Group - on the South-East corner across from Miramar while waiting to be seated. It's an amazing collection of brands across specialty home decor, furniture, and lifestyle items from lines such as Voluspa, Buster + Punch, VIETRI, NAPA Home & Garden, and Canadel.

https://ablazedesigngroup.com/store/

The beaches at the Fort Sheridan Forest Preserve are wild, rugged, and natural, featuring a mix of sand, pebbles, and large rocks rather than a manicured resort shoreline. Backed by high bluffs, dense ravines, and quiet hiking trails, the secluded waterfront offers a peaceful, scenic escape for nature lovers - amazing during the fall months. A great way to spend a morning.