Road trips aren’t just for the summer.
Before winter (and more treacherous driving conditions) really sets in, hit the road to make the most of the holiday season on one of these festive road trips.
Santa Cruise and sleigh rides in Lake Geneva
Close enough to Milwaukee for a day trip, Lake Geneva is a great getaway in any season, with the holidays giving it an extra festive boost. And according to the dating reviews website MyDatingAdviser.com, it’s the 17th best Christmas town in the country, based on 21 factors including activities, light displays, dining and hotels.
Lake Geneva offers options for all of those, beginning with Lake Geneva Cruise Line’s Santa Cruise. The cruise takes visitors on a 40-minute ride around Geneva Lake to see lighted displays on the shore and past Santa’s Secret Hideaway, where he reads the names of children who are on his nice list (and happen to be on the boat cruise, too). The adventure also includes a walk through the indoor Charities of Christmas Tree Festival, which features eight trees amid other decorations.
The cruises are offered Wednesday through Sunday, with an adults-only cruise featuring live music at 8:30 p.m. Friday and Saturday, Nov. 26-Dec. 30. Regular tickets are $20 for adults, $18 for seniors (65 and older) and $9 for kids (4-17). Prime tickets (Saturdays and other designated dates) are $28, $26 and $18. Children age 3 and under are free. For more information, see santacruiselakegeneva.com.
A handful of area restaurants and resorts offer igloos for a semi-outdoor private dining experience: Lake Lawn Resort, Mars Resort, Pier 290, Geneva National, The Ridge Hotel and Grand Geneva. Maxwell Mansion also has some larger, living-room-sized igloos for larger groups.
If there’s enough snow on the ground, Dan Patch Stables offers horse-drawn sleigh rides at the Grand Geneva Resort and Spa. Rides are offered 10 a.m. to 4 p.m. Friday through Monday and Wednesday. Rides cost $60 per sleigh, which seats four adults comfortably. For reservations, call (262) 215-5303.
Visit Dec. 4 for the city’s Electric Christmas Parade, featuring lighted floats and Santa and Mrs. Claus riding a fire truck. The parade begins at 5 p.m. at William and Marshall streets and heads through downtown along Williams, Broad and Main streets. Downtown businesses will also have holiday window displays.
Extend your stay with an overnight at the Grand Geneva. The resort's Christmas in the Country celebration includes a free trolley tour to see holiday decorations around the resort (open to guests only), a Gingerbread House Walk, Breakfast with Santa every Saturday and Sunday (through Dec. 19), and a special mailbox to send letters to Santa. Santa also has been spotted at the neighboring Timber Ridge Lodge & Waterpark. The resort also offers guests the option of having a fully decorated tree in their room for an extra charge. For more winter fun, the resort's Mountain Top ski hill is scheduled to open Dec. 12. See grandgeneva.com.
Christkindlmarket and ‘Home Alone’ in Chicago
Chicago might not be the star of a Hallmark movie anytime soon (other than as a villain, perhaps), but the benefit of a big city is there’s plenty to do, especially during the holidays. Plus, at less than a two-hour drive from Milwaukee (with good traffic luck), it’s doable as a day trip or a quick overnight.
If you’re missing the Deer District’s Christkindlmarket this year, Chicago offers two locations to fill the void: at Daley Plaza downtown and Gallagher Way in Wrigleyville. Both will feature dozens of vendors selling everything from scarves and ornaments to hot chocolate and pretzels. See christkindlmarket.com for hours.
Visit the downtown market and you won’t be too far from the city’s Magnificent Mile Lights Festival on Michigan Avenue, and the official city Christmas tree in Millennium Park, where there’s also the free McCormick Tribune Ice Rink if you bring your own skates (online ticket reservations required, skate rentals are available).
The Wrigleyville Market is part of Winterland at Gallagher Way, a festival that includes an ice skating rink ($6 for skaters age 13 and older, rentals available), ice bumper cars ($10), photos with Santa on the weekends, a Hanukkah celebration (3-6 p.m. Dec. 5) and more. See gallagherway.com.
Navy Pier will have its own festival, Light Up the Lake, with light displays, a holiday market, an ice rink, a beer garden, train rides, visits with Santa and more — all indoors. A ticket to the festival also includes a ride on the pier’s famous Centennial Wheel (which has enclosed gondolas). The event is wheelchair accessible. Tickets are $26 for adults, $21 for children (ages 3-12) and free for kids under 3. For more information, see navypier.org/light-up-the-lake.
There are lots of festive options in the city for an overnight stay. Hotel Zachary, near the Gallagher Way celebration in Wrigleyville, will host breakfast with Santa on Saturdays and Sundays, Teddy Bear Tea on Sunday afternoons, and Storytime with Chris Fascione on Wednesday and Sunday afternoons, plus complimentary Christkindlmarket mug refills. The Marriott Tribute Portfolio hotel, which opened in 2018, is named for Zachary Taylor Davis, a Chicago architect who helped design Wrigley Field across the street. For more information, see hotelzachary.com.
For a grand getaway in the city’s northern suburbs, try Deer Path Inn, which was ranked as the best resort hotel in the Midwest by Travel + Leisure this year. The hotel in Lake Forest is offering a Lost in Lake Forest Suite Experience, an ode to the Christmas classic “Home Alone,” which was set in the Chicago suburbs. The package, which is only available for the hotel’s Cornwall Suites, includes an in-room screening of the 1990 film with homemade pizza, a box of treats from Sweet’s of Lake Forest, in-room snacks including gourmet popcorn and boozy milkshakes, robes to use and take home, and gift cards for shopping in local boutiques. The hotel, which is on the National Register of Historic Places and whose building dates to the 1860s, is a modeled after a traditional English inn, with a formal English garden, afternoon tea, English cuisine in a fine dining restaurant and of course, a pub. For more information, see thedeerpathinn.com.
Rudolph stamps and Christmas trees in central Wisconsin
You could just mail your Christmas cards to Rudolph to get the town’s red-nosed reindeer postmark, but why not make a road trip out of it?
Every December, post office workers in the small Wood County village (population 433) hand stamp 10,000 cards with a special Christmas postmark that features Rudolph and is designed by local schoolchildren. Twenty years ago the town added a festival to celebrate the season on the second Saturday in December. This year’s Rudolph Country Christmas on Dec. 11 will include a 5K, live music, craft vendors, food and drinks, horse-drawn wagon rides, visits with Santa, fireworks and a parade.
The festive fun continues in nearby Marshfield, where more than 1 million lights are on display as part of the Rotary Winter Wonderland at the Wildwood Park & Zoo. There are drive-through and walk-through routes to see the display, plus first-come, first-served horse-drawn wagon rides on Saturdays and Christmas Eve. It’s free to visit, but donations for local food pantries are welcomed. The display is open 5-9 p.m. daily through Dec. 31.
Rudolph is only about 40 miles south of Granite Peak, one of the state’s best ski areas. The ski resort on Rib Mountain has more than 60 runs spread across 200 acres with a 700-foot vertical, plus four terrain parks. Lift tickets for weekends and holidays (including the week between Christmas and New Year’s Day) must be purchased in advance. See skigranitepeak.com.
Christmas isn’t Christmas without a tree. Cut down a real one at Holiday Creek Tree Farm, 438 Highway 54 W, Plover. The farm offers free rides aboard a Thomas the Tank Engine “train” (really a tractor) on weekends. The cut-your-own trees are $50, and the farm is open 9 a.m.-4 p.m. daily. For more, see the farm’s Facebook page.
If you’re in the area the first two weekends in December, you can see decorated trees during the South Wood County Historical Museum’s free Christmas Tree Walk. The museum in Wisconsin Rapids is open 12-4 p.m. Dec. 4-6, 5-8 p.m. Dec. 10, and 12-4 p.m. Dec. 11-12.
For more Christmas decor, schedule a tour at Le Chateau Bed and Breakfast/The Manor in Wisconsin Rapids. The 1889 Queen Anne Victorian mansion gets all decked out for the holidays with 67 Christmas trees and more decorations. The house is open for tours ($8 per person) by appointment 11 a.m.-8 p.m. Monday-Thursday, Dec. 1- January 15th. The bed and breakfast also has five suites available for rent Thursday through Sunday. See The Manor’s website (lechateau-the-manor-bb.business.site) or Facebook page for more information.
Christmas charm and progressive dinners in Door County
The quaint waterfront towns of Door County are even more charming during the holidays, plus a little quieter than during the busy summer months.
Door County is full of artisans offering unique gifts, but you can browse 22 in one spot at the peninsula’s first ever Christkindlmarkt in Sister Bay. Vendors will have everything from hats and candles to cookies and spices. The free market is open Dec. 3 to 5 and Dec. 10 to 12 on the grounds of the Corner of the Past Museum, 10310 Fieldcrest Road. See doorcountychristmasmarket.com.
For a dose of the outdoors, cross the peninsula to visit the Ridges Sanctuary in Baileys Harbor. The nature preserve's Natural Christmas celebration from 3 to 6 p.m. Dec. 11 will include softly lighted boardwalks, guided hikes, tours of the Range Lights, a wreath-making workshop, holiday crafts, and a decorated historical cabin where visitors can enjoy warm cider, cookies and holiday music. The event is free; the wreath-making workshop is $20. The trails of the sanctuary are otherwise open for exploring from dawn to dusk daily; trail fees are $5 and dogs are not permitted. See ridgessanctuary.org.
Head back to the other side of the peninsula for a self-guided tour (driving or walking) of Fish Creek, which has more than 70 lighted displays that are turned on nightly through February for Winter(festive) Tour of Lights.
Also in Fish Creek is Northern Sky Theater, which keeps the Christmas spirit going after the big day with “Home for the Holidays,” featuring classic holiday songs, originals and humor. Performances are held inside the Gould Theater in Fish Creek at 4 p.m. Dec. 27-31. Tickets are $30 for adults, $20 for students and $15 for kids 12 and under. See northernskytheater.com.
For more decorations (inside), head to the Door County Maritime Museum in Sturgeon Bay. The museum’s Merry-Time Festival of Trees features dozens of decorated trees throughout the museum, which is open 10 a.m. to 5 p.m. daily through Jan. 2. The museum will also play host to the Jingle Mixer Gala Dec. 14, with live music, auctions, appetizers and drinks. See dcmm.org.
Go dashing through the snow on a Winter Wine Tour & Sleigh Ride with Door County Trolley. The 4.5-hour tour includes a half-hour horse-drawn sleigh ride and rides aboard a heated trolley to a wine tasting, a bonus stop and a fireside lunch. The tours are offered at 10 a.m. Saturday, December through March (no tour on Christmas or New Year's Day, extra tour on New Year's Eve). Tickets are $76.95. See doorcountytrolley.com.
If you’re visiting to ring in the New Year, do it in Sister Bay for the annual Cherry Drop, an ode to the peninsula’s favorite fruit. The evening includes fireworks at 8 p.m. at the Sister Bay Ice Rink, music downtown at The Garage, and the countdown to midnight that culminates with dropping a giant lighted cherry.
There are plenty of cozy B&Bs, inns and other lodging options in Door County, but two offer a special holiday experience. Stay at the Thorp House or White Gull inns in Fish Creek the first three weekends in December or Jan. 7-8 and you can take part in a weekend-long progressive dinner. The weekend includes horse-drawn carriage rides and appetizers on Friday and a four-course dinner on Saturday. The package costs $121 per person (plus the room cost, two-night minimum required). Breakfast is included at both inns. See whitegullinn.com or thorphouseinn.com.
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This article originally appeared on Milwaukee Journal Sentinel: Road trips in Wisconsin and Illinois, from Lake Geneva to Door County