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General Features
Home›Featured-Blogs›General Features›Weekend getaway ideas from our Park Ridge Insiders

Weekend getaway ideas from our Park Ridge Insiders

By Trent Modglin
August 16, 2025
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Door County, Wisc.

Got a few days free and looking for an ideal weekend getaway spot? We tapped into the minds of some of our previous Park Ridge Insiders for ideas on where to go

Wisconsin. I enjoy all that state has to offer (save for the Packers). Our top spot is Door County (read our feature here), specifically Sister Bay, and the free music offered along the waterfront on different weeknights in the summer. Also The Cove or Lake Lawn Resort for shorter getaways in the Lake Geneva area. Cafe Benelux or the 3rd Street Market Hall hit the spot when we see concerts in Milwaukee (read out feature here) every year.

— Zach Haycraft

Delavan, Wisconsin is our go-to escape. Boating, swimming and enjoying the lake life — it’s the perfect recharge and change of scenery. Our go-to spot for coffee and breakfast sandwiches is Boxed & Burlap. Their sausage, egg and cheese sandwich is amazing. Our hidden gem for dinner is The Duck Inn supper club, which serves a great king cut prime rib and a delicious brandy old fashioned. Kishwauketoe Nature Conservancy in nearby Williams Bay is a great spot to go for a hike that starts in a wooded area and then opens up to a prairie.

— Joe Breisch

Pfister Hotel in Milwaukee

If we get 24-48 hours to ourselves, we tend to go to Milwaukee (read our feature here) to visit my sister and her crew. Milwaukee is a great spot for families looking for a weekend away. It is easy to get around and has options for all ages. A stop at the Pfister Hotel is one of our all-time favorite activities. Irish Fest every summer is a must too.

— Mary Connolly

Boston. I love to pop in for a Red Sox game and some awesome Italian food in the North End. For a romantic weekend, head to Anaway Place (cabin rentals) in Wisconsin. It’s wonderful, especially in the fall.

— David Cartwright

New Buffalo, Michigan. My perfect day there is hiking in the morning, lunch at Beer Church Brewing Co. and a bonfire on the beach for the sunset.

— Lisa Kay Kovilic

Lake Geneva

Lake Geneva. It’s close, and there is lots to do — shopping, good bars, good food and beaches. I love Simple Café up there and the bakery next to it. … I also have fallen in love with the Anderson Japanese Gardens in Rockford. I took my grandma there and just walked around and soaked it all in. You can feed the geese and koi, and it’s so beautiful to walk through anytime of year.

— Dania Garcia

Every Saturday through November, there is a farmers market surrounding the capital building in Madison called Saturdays on the Square. It is so relaxing to go and stay for the weekend, do some shopping and then go for a hike.

Madison, Wisconsin. Every Saturday through November, there is a farmers market surrounding the capital building called Saturdays on the Square. It is so relaxing to go and stay for the weekend, do some shopping at the market and then go for a hike in one of the beautiful areas surrounding Madison. There is a lake where they have kayak rentals and so many shops and restaurants. If you are looking for an excellent burger and beer, The Old Fashioned is a great choice for a sit-down meal.

— Erica Juris

Northern Wisconsin, especially the Minocqua area, holds a special place in our hearts. We look forward to our time there when we can unplug and enjoy the simple life for a bit.

— Matt Hachigian

Swissotel in Chicago — photo by Kevin Kaminski

I enjoy taking my daughter into the city for a “Chicago staycation.” I find a good rate for a room at a nice hotel, and we order room service and walk around the city. If we don’t stay the night, we bring our dog down to the dog beach or go on a Chicago boat tour when they have a pet-friendly day. The best hotel experience we’ve had yet was at the Swissotel on Wacker Drive. They provide the room with activities based on the age of your children. In our case, there were coloring books and board games!

— Stefanie Caito

But I do love hopping on the Metra and heading into Chicago for the day for a Cubs game. Or brunch and day drinking at Federales in the Fulton Market district, where you do a shot of tequila and get to throw the empty ice glass at a bell. I usually miss. The bottomless sangria and brunch at Lil’ Ba-Ba-Reeba in River North is fun too.

— Natalie Amabile

Every year we take advantage of our Harvest Hosts membership, where you can camp out at various breweries, distilleries, wineries, farms, golf courses, even museums.

My family owns an RV, so we love getting out to Wisconsin or Michigan as often as possible, and every year we take advantage of our Harvest Hosts membership, where you can camp out at various breweries, distilleries, wineries, farms, golf courses, even museums. Modales Wines in Fennville, Michigan is a personal favorite.

— Steve Judge

Downtown Galena — photo by Enjoy Illinois

I love going to Galena. We had a home up there when I was growing up, and I still love visiting. The shops are wonderful, and I love hiking while I am there. There is so much to do in the area.

— Meghan O’Neill

Door County (read our feature here) in Wisconsin. It’s perfect for those who enjoy hiking, biking and exploring the scenic coastline of Lake Michigan. It also offers a rich cultural experience with its unique local arts, delicious cuisine and historic lighthouses.

— Milena Bulic

I like exploring all the little towns in southwest Michigan like St. Joe’s and South Haven, but the lakefront in Chicago is where it’s at for me.

I like exploring all the little towns in southwest Michigan like St. Joe’s and South Haven, but the lakefront in Chicago is where it’s at for me. … I love going into the River West neighborhood to have dinner on the patio at Piccolo Sogno or rub elbows and enjoy authentic rustic Italian at La Scarola.

— JoAnn Fosco

We haven’t had a weekend getaway in a while, but as soon as we secure some babysitters, we plan to check out The Fields of Michigan. It is a luxury glamping experience in South Haven — only about a 2.5-hour drive. We have heard really good things. You rent a tent that has a king bed, electricity, flushing toilet and hot water. Oh and, there is a spa on site… that’s our kind of glamping!

— Dr. Julie Davis

The Fields of Michigan

Tags3rd Street Market HallAnaway PlaceAnderson Japanese GardensBeer Church BrewingCafe BeneluxDelavan WisconsinFederales ChicagoFulton MarketHarvest HostsKishwauketoe Nature ConservancyLa ScarolaLake GenevaLake Lawn ResortLil' Ba-Ba-ReebaMadison WisconsinMilwaukeeModales WinesNew BuffaloPfister HotelPiccolo SognoRiver West ChicagoSimple Cafe Lake GenevaSouth HavenSt. Joe's MichiganSwissotel ChicagoThe Cove Lake GenevaThe Fields of MichiganThe Old Fashioned WisconsinThe Real Park Ridge
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The Real Chicago — an eye-catching, family friendly entertainment magazine for active locals and tourists — originally launched in 2006. It now has a sister publication: The Real Park Ridge. Proud to be servicing our new home in Park Ridge, as well as the surrounding areas of Rosemont, Niles, Des Plaines, Mt. Prospect and NW Chicago.

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