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Family Travel


Harvest festivals, cider tasting, and crunchy forest trails. We’re loving the cool fall evenings and rediscovering our local parks in their new finery—with the top Midwest vacations for some autumn splendor and fun fall activities.

Best Midwest Vacations In The Fall

This roundup includes small towns with lively hearts and big, bold cities where anything goes. In the fall, these places offer up colorful landscapes (whether they’re urban or rural) plus a range of festivals and events themed for the autumn season.

Whether you favor compact cabins, stylish condos, or multi-story townhouses, book yourself a rental home on FlipKey to come back to after a day of autumnal adventures. Rentals make sense in terms of cost, space, and independence, meaning you end up with a great Midwest vacation trip that’s tailor made for you.

Here’s our 10 top towns and cities in the Midwest where you can pick a pumpkin, try a tasting, and see some fantastic seasonal scenery.

Hocking Hills, Ohio


“Everything was there. The kitchen was fully stocked with pots, pans, cups, glasses, plates, etc. Bedrooms/bathroom clean as can be. It was like coming into your own home.” — FlipKey Reviewer

Book yourself a cabin and set out to enjoy fall in Hocking Hills. Kick off at Old Man’s Cave, named after a local hermit who made this spot his home, and take advantage of the area’s excellent hiking terrain. Swing by the Circleville Pumpkin Show, with its parades, contests, and stalls selling all the pumpkin-based foods you can think of, and then some.

See all FlipKey rentals in Hocking Hills!

Kansas City, Missouri


Kansas City offer several fall festivals and events. If you’ve got the family in tow, check out the Great Pumpkin Fest at the Worlds of Fun amusement park, where there’s a hay bale maze and kids’ pumpkin patch. You could also try Kansas City Zoo for beer and wine tasting, Halloween-themed events, and of course, plenty of animal fun.

See all FlipKey rentals in Kansas City!

Custer, South Dakota


Stay in this quiet mountain town and you’ll have the fall foliage of the Black Hills National Forest right on the doorstep. Climbing, hikers, motor-bikers—they all come here to enjoy Custer’s historic center and the views from the roads and trails around it. Make sure you seek out the passageways and caverns of the Jewel Cave National Monument and the iconic profiles of Mount Rushmore.

See all FlipKey rentals in Custer!

Des Moines, Iowa


Image courtesy of TripAdvisor. © Kasal Was Here Productions.

Start at Geisler Farms, with s’mores over a fire pit, then pick your way through the corn maze, and choose your own pumpkin to take home. Des Moines has more than 800 miles of trails to explore on foot or by bike, leading you around the city’s fall foliage and further out into the glorious Iowa countryside.

See all FlipKey rentals in Des Moines!

Galena, Illinois


Start your tour of Galena boating down the mighty Mississippi River, watching leaves on the turn, or fishing for bass and catfish. You might prefer the aerial view from a hot air balloon with Galena on the Fly, or the arts and crafts at Galena Country Fair, amid the gorgeous autumnal setting of Grant Park. In the evening, try Matthew’s Haunted Pub Crawl for a ghostly local tour washed down with a few drinks.

See all FlipKey rentals in Galena!

Wisconsin Dells, Wisconsin


“Our condo worked out perfectly for us for the vacation. We loved having the water park on site! Everything was very clean and any request we made was addressed very quickly. Would highly recommend!” — FlipKey Reviewer

The Waterpark Capital of the World is understandably popular year-round, but there are plenty of other things to do here. In the fall, board Dells Boat Tours to appreciate the beauty of the Wisconsin River and the Dells rock formations. The views are arguably even better on the sunset cruise, which comes with dinner provided. This is also a good time of year to zipline through the treetops and see those changing colors up close.

See all FlipKey rentals in Wisconsin Dells!

Ann Arbor, Michigan


This lively college town has plenty in store in the autumn. Begin with a self-guided tour of Matthaei Botanical Gardens and Nichols Arboretum, bursting with shrubs and trees, and truly breathtaking at this time of year. Nearby Dexter hosts the Apple Daze festival, with hayrides, a pie-eating competition, and plenty of cider to toast the new season. Lest we not forget the main draw in Ann Arbor: The University of Michigan football team. Experiencing a game at the Wolverine’s stadium—the largest in America with a capacity of 111,000 (!) people—is a memorable experience.

See all FlipKey rentals in Ann Arbor!

Minneapolis, Minnesota


“This property has everything you could need, including anything you might have forgotten. The atmosphere is lovely… We rented bikes from the owner, picnicked in the backyard under the sunshade, walked to groceries, restaurants, and coffee, biked to the beach.” — FlipKey Reviewer

Don’t miss the lovely Minnesota Landscape Arboretum, with its seasonal scarecrows, Sensory Garden, and Pumpkin House. If you’re already getting into the Halloween spirit, you might want to bag a ticket for October’s Zombie Pub Crawl, where you’ll be able to taste the best of the excellent Minneapolis craft beer scene (in full zombie garb).

See all FlipKey rentals in Minneapolis!

Traverse City, Michigan


Warm days, cool nights, and leaves crunching underfoot. This is a great time to book a rental in Traverse City, where you’ll find entertainment in the museums and casinos, and plenty of fall color around the inland lakes and on the sweeping drives from winery to winery. Taste farm-to-fork flavours at a local restaurant, catch your own meal from a fishing boat, or take off on a biking excursion among gorgeous autumn scenery.

See all FlipKey rentals in Traverse City!

Nashville, Indiana


“We loved everything about this place. It was in a perfect spot—not far from town, but out of the craziness. The owner was great to deal with, the place was very clean, and it felt like a home away from home! Beautiful setting and backyard, and everything we could possibly need was provided.” — FlipKey Reviewer

By day, admire the colorful landscapes of Brown County, catching the changing leaves of Yellowwood State Forest and Brown Country State Park. In the evening, you can see a bluegrass show, grab a first-rate Nashville dinner, and round the night off in a hot tub.

See all FlipKey rentals in Nashville!

Family vacations are great opportunities to create memories that last a lifetime, but painful travel experiences can generate unpleasant memories that never fade. Neverending car rides and missed flights can ruin otherwise fun trips. In my own travels, I have always avoided layovers in Denver because I still remember playing on the moving sidewalks until I was bored and irritable during two extended layovers in Denver International Airport. I’m sure my dad wished we were anyplace but a large, busy terminal for those seemingly endless delays. These days, even a routine flight can involve long delays at the airport thanks to increased security and reduced staff at check-in. So how do you keep the kids happy on the fly?

While you can never guarantee a trip free of delays and mishaps, you can nevertheless plan the best way to handle those situations when they arise. To help ensure good travel memories and smooth vacations, we’ve put together a list of the best kid-friendly airports for long layovers. These airports provide more than just moving sidewalks to keep the kids busy. Kid-friendly amenities include everything from aviation-themed play areas and educational exhibits to private family rooms and rocking chairs for mothers with infants.

We judged these airports based on their kid-friendly amenities, convenience as a stopping point, and proximity to great family vacation spots. Next time your family takes to the sky, plan for the unexpected by connecting through these family-conscious hubs.

San Francisco

SFO AquariumWhile San Francisco is a common endpoint to a journey, it can also serve as a great connection to Asia-Pacific destinations like Hong Kong, Seoul, and Tokyo. Before stepping onto a long trans-Pacific flight, there are few airports better suited to entertaining kids than SFO.

The airport includes nurseries in Terminals 1, 2, and 3; Kids’ Spot play areas in three locations, and three different aquariums in Terminal 1 before security. Dedicated family lanes also help families get through security at their own pace. The convenient security lanes can be helpful on very long layovers, as SFO’s location makes it relatively easy to escape the airport and explore San Francisco for an hour or two between flights.

A-List Mom Travel ranked SFO the second best airport terminal for kids (after O’Hare). They point out that the airport has great options for older kids and parents in addition to the play areas, including the Commission Aviation Library and the 11,500 square foot Louis A. Turpen Aviation Museum. The museum, “conjures up a feeling of a bygone era when traveling was a sophisticated pastime for only the rarefied few.”

SFO is so dedicated to keeping your family happy and engaged between flights that they have put together self-guided tours of the airport terminals. The tours will lead you and your kids to the various exhibits, play areas, and airport features that make SFO unique. They also include questions and challenges to occupy the little ones. There’s no better way to spend a long layover than taking the family on a treasure hunt.

Boston Logan

Logan KidportIf you are taking the kids out of the country, then Boston’s Logan International Airport is a great place to catch your flight. The domestic and international terminals are connected by walkways, so transfers are quick and easy. The most popular international flights from Boston connect with European hubs London, Frankfurt, and Paris, though you can also fly direct to Tokyo and Beijing.

Families facing a layover in Boston will find the airport well-equipped to keep your kids entertained. Two Kid Port play areas, created with the Boston Children’s Museum, are located in Terminals A and C. Like O’Hare, Logan’s indoor playgrounds feature plane and tower shaped climbing structures. These play spaces also include seating for parents, as well as an area for watching TV. Atlanta-based blog, My Busy Children, advises, “I would definitely recommend waiting for the airplane there with kids instead of the gate area.”

Keeping the youngest jet setters in mind, Logan also features rocking chairs, family restrooms, and rooms for nursing mothers who want some space and privacy.

In addition to major domestic and international flights, Logan is also a hub for transportation to regional vacation destinations like Cape Cod, Vermont, and Maine.



Read more about Phoenix airport here.


YangchuanosaurusAtlanta’s Hartsfield-Jackson airport is the busiest airport in the world, and also one of the coolest airports for kids to visit (it came in first for amenities and third for families on a recent Travel Leaders Group poll cited on Gadling). Why? Dinosaurs. In addition to its two play areas, the Atlanta airport features a fully assembled skeleton of Yangchuanosaurus—a dinosaur that lived in China during the Jurassic period. This particular dinosaur now lives in the Hartsfield-Jackson Atrium, to the amazement of children and parents passing through.

Hartsfield-Jackson also features an Airport Art program that includes artworks and rotating exhibits that delight passengers of all ages. The Youth Art Galleries on concourses D, E, and T display art projects by Georgia students.

Atlanta is a major hub for Delta, and the most popular domestic flights connect with many cities in Florida, New York City, and Dallas, along with international hotspots like Cancun, Jamaica, and Nassau.

Keep in mind that Hartfield-Jackson is an enormous airport, and more than a few travelers have gotten lost in its concourses. While it’s one of the better airports for keeping the kids busy, you should also make sure your children don’t stray far, and remember to leave plenty of time to get from play areas and exhibits to your gate before your flight leaves.

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by Jenn & Hannah

It is a great time to take the family skiing! If you’re headed to the East Coast, New Hampshire is a natural choice for enjoying winter fun in the White Mountains. Everyone is familiar with the well publicized (read that very expensive) big hills with lodges and hot tubs, but there are other budget stretching options! With little kids, you probably don’t need six world class black diamond runs and an enclosed heated lift as much as you need affordable child care and lift tickets that are budget friendly! Here are three options that fit the bill:

Pat’s Peak 

Located in Henniker, NH, Pat’s Peak is a family run outfit with a variety of winter fun on tap, from tubing to skiing, snowboarding and snow biking too! Their nursery is small, with an excellent child-care giver ratio. Reservations are recommended. With long, slow, sloping green hills that run from the top of the mountain down, this is a great place to teach kids to ski. They’ll be able to get off of the “bunny hill” quickly and experience success. With full day lift tickets for adults under $60, and discounts for ticket bundle deals, everybody wins. This is where we taught our four kids to ski, and it’s my first pick for value and a family friendly atmosphere. That they are adherents to the Sustainable Slopes Charter is just a bonus!

Mount Sunapee 

Located in Newbury, NH, Mount Sunapee is a wonderful place to take kids! They have a full service childcare program for children up to five years old and an array of lessons for all ages. Reservations are recommended. Kids five and under ski free with a ticketed adult, and with eight lifts there are plenty of choices for skiers of all levels. Unlike Pat’s Peak, they have “ski and stay” packages arranged with local inns that include a lift ticket and breakfast, which is very convenient for families traveling to ski.

Ragged Mountain

Ragged Mountain, in Danbury, NH, is where we took our kids when they’d mastered the basics and were ready for the next skiing challenge. Unlike some other hills, which begin childcare with one year olds, Ragged Mountain has a daycare program for babies as young as six weeks old, which is extremely convenient for nursing mothers! With a range of discounted lift ticket deals adults can ski for as little as $31 per day, mid week. Ragged Mountain also boasts an array of slope side lodging, from fully equipped, self catering apartments, to bunk rooms where you can stay for as little as $20 per person per night. Think of it as a skiing hostel!

Don’t miss the opportunity to ski with your family this winter. Snow is more than a chore to be shoveled, it’s winter’s greatest play thing! Pack your kids, pack your sense of adventure and hit the slopes!

A dynamic mother-daughter duo of travel writers, Jenn & Hannah are in their fourth year of an open ended world tour. Their partners in crime are Dad & 3 brothers and together they are http://www.edventureproject.com

by Jenn and Hannah Miller

Rolling into NOLA during Mardi Gras, the day of the Saints’ Superbowl Parade with a van full of kids might not seem like the height of good family travel planning, and to tell the truth, it wasn’t. It was a complete accident! Nonetheless, it was one of the best travel experiences our family has had and one our kids are not likely to forget!

Where to Stay

There are lots of options in NOLA and most of them are either booked solid or extremely pricey during Mardi Gras. Our favorite option, no matter where in the world we’re traveling is to rent a house or an apartment. When we discovered that fully furnished & equipped rentals were available anywhere in the world for far less than a hotel stay with our four kids, it revolutionized our travel experience. FlipKey has 24 rentals available in New Orleans, in case you were wondering! Whether you’re a family of two or ten, you’ll find one that fits! The ability to cook for yourself, is an added money saving bonus with kids!

Today we’re featuring a post from another inspiring traveling Family. Jenn Miller and her family have been on the road, living it up and keeping us up to date at the Edventure Project.

by Jenn Miller

Our mornings are all very different, and yet, delightfully the same, no matter the continent or country. Children wander from tents or hammocks, beds or boat bunks. Tea is brewed. The day’s adventure begins. Every morning I remember; this is why we live this life: Because it’s about the people, memories & moments, not things. Our life is lived without a clock, without cubicles or classrooms and on our own terms.

Almost four years ago we sold our house and our stuff, quit a six figure job, packed up our four children and hit the road. The idea was to take a year “off” and bicycle from London, England to Tunisia and back. Somewhere in there, our gap year became our life and the Edventure Project was born.

Why would someone do that? Especially with kids?!

There are lots of families that do, and I can’t speak for all of them, but for us, these five reasons just about sum it up:

1. Love People, Not Things

This is a mantra we repeat often to our toddlers and try to live out as a family. It guides so many of the choices we make, including the choice to travel as a way of life. We’ve intentionally chosen to spend our lives building relationships with each other and with our children, full time, instead of investing the time in jobs, projects or pursuits that would send us chasing other directions after other things.

Whether your family’s summer was full of baseball games, fishing at the lake, or just hanging out with friends, I hope it was like ours: a grand reprieve from the structure and routine of the school schedule. I know—summer’s not officially over until the Fall Equinox in late September, but that’s just a technicality! Ask any kid and they’ll tell you summer winds down on Labor Day Weekend.

In some ways September is more a New Year’s event than January, especially for families with school-age kids. It’s a fresh start with new teachers, a new set of classmates, and a whole new set of goals and challenges. Labor Day weekend offers a perfect opportunity to say farewell to summer while kick-starting the school year. Instead of another trip to the lake or another relaxing picnic gathering, families can embrace the upcoming school year with an urban weekend that jumpstarts the brains after a long lazy summer, and fills the closets with back-to-school gear.

Midwesterners have an easy choice for a Labor Day urban getaway: Minneapolis is easy to get to and easy to negotiate, with great vacation rentals and more than enough culture to engage the whole family. Whether your family gravitates towards art, science, or theater, you can find it on Labor Day Weekend, plus fill in the gaps with great shopping.

Spend an afternoon meandering the Minneapolis Institute of Arts for a look at how people have expressed themselves across the globe and through time, from African masks to Japanese scrolls. Then go big and head over to one of my favorite spots, the Walker Sculpture Garden, where the Standing Frame sculpture frames the city scenes and Prophecy of the Ancients frames the sky. The sculptures in this garden aim to change your perspective on the world, and one way or another they do succeed.

Across the river in St. Paul, the experiment gallery in the Science Museum of Minnesota is a favorite destination for kids of all ages, followed by a visit through the dinosaur and fossil exhibit. The best reason to go to this science museum over Labor Day?  It’s the last chance to walk like an Egyptian through the King Tut exhibit – it closes right after Labor Day.

If your family is more into Shakespeare than mummies, here is a good option: take in a performance of Hamlet, a modern take on the classic story, at the Jungle Theater in Minneapolis. After which you might ask… “To shop, or not to shop?” and the answer will definitely be “Shop!” Without a doubt, you’ll want to give yourselves a full day for the Mall of America, where you can break up the shopping with adrenaline-charged roller coaster rides and flight simulator experiences, or head for a quieter diversion in the aquarium.  Whichever activities you choose to fill the urban getaway, it’ll add up to a great transition back to the new school routine, and maybe will even become a family tradition.

Suzanne Johnson lives, writes and plays in the Cascade mountains of Oregon with her family of adventure-prone boys. More of her writing can be found a SuzanneMyhreJohnson.com.

By Bethaney Wallace

When I was in grade school, each new school year presented the opportunity to recount what I had done during the summer months. When classes resumed I was asked to describe what I had been doing with my time away.  The grade usually correlated to the amount of work that was required: in kindergarten I gave a show and tell presentation; in the sixth grade, I wrote an essay.  Each fall I would tell my teacher the same thing: I told them about my summer vacation.  Sightseeing at the Grand Canyon, building sand castles on the beach, or navigating our way through Disneyland – my family always went on a vacation.  It was a bonding experience, my parents said, and we were required to spend at least an entire week together – whether we were to be cramped in a single cruise ship cabin or lounging in an entire rented cottage – the time was to be spent together.

The first vacation I have memories from is when I was five years old and my parents, baby sister and I went to the Lake of the Ozarks.  I may not remember much of the scenery, or any of the lake for that matter.  But I do remember listening to the neighborhood band play in the park while I climbed the jungle gym.  I remember going to day camp and creating my own bejeweled hat while my parents were off doing boring adult things.  For anyone who debates sending their children off to day camp programs, it was the highlight of my trip.

Since that initial vacation, my family has traveled to a new location each year.  Each destination was a new place to explore and buy tacky souvenirs to bolster our vacation T-shirt collection: one for every location.  During my teenage years I was a little less enthusiastic to oblige my parents’ vacation plans, but by the time I hit college I was begging them to extend the trips a day or two longer to enjoy the momentary respite from studying and the less than desirable college dining hall food.

Why should your family travel together?

Vacations aren’t just to “get away from it all” or for the relaxation. In fact, anyone who has ever gone on a family vacation – especially with young children – can tell you they are often far from relaxing.  What family vacations do provide is an unparalleled bonding experience.  Sharing new and exciting experiences with your family connects you in a way that few other events allow.  The activities, the meals, even arguing over who was at fault for getting lost are moments that you and your family will always cherish.

Enough with the gushy stuff.  When it comes down to it – even with the budget restrictions, the challenges of traveling with youngsters, or the stress of planning – in the long run, family time trumps all the obstacles.

This summer, my family went to Chicago, and due to work conflicts I wasn’t able to join them for the first time since our summer family vacation initiative began.  They showed me pictures and brought back my obligatory keepsake (a poster from Wrigley field).  But I missed out on the road trips; I missed out on arguing over what we were having for dinner, or what museum would have the best exhibits;  I missed out on all of the fun.

Next summer, when my parents schedule our annual trip’s destination and dates, I will take off work months in advance. When I return and my boss asks how my trip was, I’ll give my vacation presentation, the same way I did in elementary school.  Family vacations are an important part of my life, I’ll tell him.  And I have the T-shirts to prove it.

Bethaney Wallace is a social media advocate for the mortgage rates website, MortgageSum.  She is passionate about blogging and family vacations.