5 Family-Friendly Fall Weekend Getaways For Under $500

As the leaves start to change color and temperatures begin to cool down, families may be itching to get out and enjoy the fall season together. However, weekends can get hectic with activities, sports, and other commitments. A short drive away, there are many affordable family-friendly getaway options for a relaxing fall weekend that won’t break the bank. Here are 5 ideas for family fall escapes that can be enjoyed for under $500 total.

Lumberjack Country in northern Wisconsin

Head up to northern Wisconsin for a true lumberjack experience surrounded by the beautiful fall colors. The city of Hayward is located right in the heart of “lumberjack country” and offers several activities perfect for a cozy fall weekend. Start your weekend with a tour of Lumberjack World Championships park which features a variety of lumberjack games and events like log rolling, axe throwing, and more. Even off-season, you can see demonstrations of these lumberjack skills.

Spend time exploring the trails around Hayward that wind through scenic maple forests. Keep an eye out for colorful birds and wildlife as you stroll through nature. For a memorable meal, stop at the Sandy Point Restaurant overlooking Lake Hayward. Enjoy tavern-style dishes like applewood smoked pork chops or homemade pizzas by a roaring fireplace.

In terms of lodging, check into the American Birkebeiner Trailside Lodging located just 5 minutes from Hayward downtown. Their comfortable cabins have kitchenettes starting at just $99 per night on weekends. The total estimated cost for two nights of lodging, tours, and meals for a family of four: $450.

A cozy cottage getaway in Door County

Only a few hours’ drive from Milwaukee or Chicago is the picturesque Door County peninsula jutting out into Lake Michigan. Known for its bucolic scenery, lighthouses, and cherry orchards, it’s a quintessential fall destination. Book a charming waterfront cottage like those available through Door County Lodging which has options from $199 to $299 per night on weekends in the fall.

With your cottage as a home base, spend a day exploring nearby spots like Washington Island Ferry Crossing or Cave Point County Park hiking trails. Stop into local orchards and farm stands to pick your own apples, pumpkins, or seasonal produce. Indulge in Door County’s signature cherry pie or fish boil from local eateries along the scenic shoreline. The total estimated cost for a two-night waterfront cottage stay, activities, and meals for four: is $480.

Fall fun in Galena, Illinois

With a quaint Main Street lined with shops, inns, and restaurants, Galena offers a picturesque fall small-town escape only a few hours from Chicago. Stay downtown at the cozy DeSoto House Hotel from $139 per night on weekends. Their breakfast pairs perfectly with views of Galena’s historic architecture.

While in town, browse the shops carrying unique gifts or grab a pumpkin spice latte from a local café. Nearby sites like Grant Home and Galena Cellars Winery are perfect for learning about Galena’s history and sampling wines. End the day with dinner along the Mississippi River downtown at places like The Lil' Inn offering satisfying seasonal specials.

Book a wagon or carriage tour through Galena offered by companies like Galena Trolley Works for around $18-28 per person. Admire the colorful scenery as you learn more about this charming town. With ample shopping, food, and activities to choose from, a family can easily enjoy a memorable fall weekend exploring Galena for around $450 total.

A leaf-peeping getaway to New England

Vermont, New Hampshire, and Maine offer some of the most stunning fall foliage displays in the country each October. A road trip allowing the ability to see colors change is incredibly memorable for families. Begin your foliage tour in northern Vermont, exploring Waterbury for cheese tastings followed by a hike up Mount Mansfield to take in vistas of fiery landscapes.

Continue through New Hampshire’s White Mountains stopping in North Conway known for shopping and as a fall foliage hotspot. Head over to Portland, Maine, and check into The Portland Harbor Hotel from $199 per night on weekends. Ride a ferry from downtown to explore the Casco Bay Islands or drive an hour north to Acadia National Park for scenic ocean vistas. Total costs for the 3-day, 2-night road trip including lodging, snacks, tolls, and gas would be under $500 for a family of four.

A relaxing getaway to the Wisconsin Dells

An iconic Midwest destination, the Wisconsin Dells is known for world-class indoor and outdoor water parks perfect for all ages. However, come fall, kids can still have fun while parents unwind without the summer crowds. Check into a resort like The Wilderness located right on the river, boasting rooms from $129 per night on weekends in the fall. They offer amenities like indoor pools and activities kids love.\

Spend one day exploring attractions like animal shows, mini golf, or Mirror Lake State Park trails. At night, families can enjoy activities like The Dells Duathlon with a scavenger hunt in the woods or a pumpkin patch festival downtown. Other days are perfect for relaxing on scenic nature hikes, fishing or boating excursions. Meals are easily enjoyed at various restaurants downtown. All in for two nights of lodging, activities, and meals for a family of four comes to under $500 this time of year enjoying the best of the quieter Dells season.

Whether looking to experience colorful countryside scenery, charming small towns, or more action-packed adventures, these affordable fall weekend getaways are perfect for families ready to create lasting memories in the crisp autumn air. With scenic natural beauty, quaint attractions, and a relaxed pace, each destination allows bonding time away without breaking the budget. Grab your sweaters, load up the car, and start planning your getaway to enjoy everything fall has to offer across the Midwest and beyond.