14 cities that give you the worst case of FOMO

Estimated reading time: 15 minutes

Looking at cities that have a lot going on

You know that feeling you get when you when you’re in the middle of having fun, but get this sinking feeling that you’re missing out on something even better? It’s like when you’re enjoying a delicious meal, only to look across the table and see what your partner ordered, and immediately regret your decision and feel the ultimate food envy.

That paranoid feeling has earned the name FOMO, fear of missing out.

Because we have so many decisions to make, and social media is always there to show us what we missed out on, it’s impossible not feel even just an inkling of FOMO every now and then. While we’re all about staying true to our decisions and enjoying the moment regardless of where we are, sometimes FOMO is inevitable.

In fact, when it comes to traveling, we found that there are entire cities out there that will give you a case of FOMO. Don’t let that scare you away though; a good FOMO flare up simply means there are so many things to do and places to see, that you’ll have a hard time choosing between all the epic events and attractions. Too many options has never been a bad thing, especially when you’re exploring a new city, so take a peek at our list of FOMO-inducing destinations, and good luck deciding on what to do first!

Boston, MA

Buckle up for springtime in Boston, because it’s going to be crazy! Crazy busy, that is. March and April bring with it some of the most legendary events around Boston, which is great, but we’re not going lie, it really raises the FOMO stakes. As the temperatures rise, so do the number of events in the state capital—are you ready for it?

If you’re ever going to celebrate St. Patrick’s Day outside of Ireland, Boston is the place to do it. The city turns a shade of Kelly green come March 17, when all kinds of Irish celebrations hit the streets and venues, from the Celtic Sojourn to the South Boston Parade. Around the same time, the spring session of Dine Out Boston kicks off, further giving you a taste of the city, as participating restaurants serve prix fixe menus.

Then comes April. The Red Sox step up to plate for their first home game at Fenway Park at the beginning of the month; something fans have marked on their calendars and bought tickets for months in advance. The Sox also play a home game every Patriot’s Day. Off the field, the historical anniversary of the Lexington and Concord Battles is commemorated with re-enactments, a lantern lighting, and a parade. Every year, the Boston Marathon falls on Patriot’s Day, too, meaning you may find yourself splitting your time between battle fields, finish lines, and baseball mounds. Is now a good time to mention that ArtWeek rounds out the month, too?

San Diego, CA

Oh, San Diego, you are forever a FOMO instigator. From your sunny beaches to your brewery scene, you always have us wondering what kind of fun we’re missing out on—and that’s before you even add in your event calendar! July in SD is particularly insane, with several iconic festivals happening either back to back or at the exact same time—how is one to choose?

Everyone counts down to San Diego Pride, as the Hillcrest neighborhood becomes a rainbow-streaked party in support of the LGBTQ community. This year, the Pride celebrations began mid-July, but that just happened to coincide with both the IB Sun & Sea Festival and the second weekend of the Over-The-Line Tournament. Pirate parades and sand castle contests at the IB event or beach softball games on Fiesta Island?

This year, the FOMO only got stronger the following week, as Comic-Con took over downtown. Whether you attend the event or not, everyone finds pleasure in seeing the entire city become inundated with comic fans dressed up like their favorite super heroes, anime characters, and villains. At the same time, the Heroes Brew Festival was simultaneously taking place down at Waterfront Park, another event in which heroic costumes are strongly encouraged. The possibilities are practically endless in this beach town, so stick to your plan, and just try not to think about what else is going on—easy peasy, right?

Little Rock, AR

Little Rock knows how to do autumn. With foodie fests and state fairs happening all throughout October, it puts on a good show, meaning it’s not going to be easy to prioritize which places to check out first. Some of the best events on the roster will make your belly happy, so pack your stretchy pants, and prepare to chow down!

For the best possible experience in Little Rock, you’ll want to bring a healthy appetite. We’re talking a huge, month-long foodie affair, with snack-centric festivals, including the Main Street Food Truck Festival in the beginning of the month, followed by the Arkansas Cornbread Festival, and last but not least, the Annual World Cheese Dip Championships! You heard that right, contestants will be competing for the Big Dipper title, the first-place cheese dip award. If your taste buds are willing to linger until early November, you can even take a bite out of Chili Fights in the Heights, a chili cook-off and charity event.

There’s no chance you’ll enter hanger territory, as even the Arkansas State Fair hosts its own fair share of grub. Who doesn’t love caramel apples and funnel cake? This 12-day extravaganza presents concerts, livestock shows, carnival rides, and more, making you feel like a kid again. With some many things to do in Little Rock, will you be able to fit it all in?

Breckenridge, CO

Breckenridge was made for winter. Its five mountain peaks and solid snow fall are undeniably appealing, but the rugged city also knows how to throw a winter party or two (or four!). Between December and January, Breckenridge closes out the old and opens the new year with a number of gatherings that will leave you pressed to prioritize.

Eager to spread the holiday cheer, the city hosts its annual Lighting of Breckenridge and Race of the Santas during the first weekend in December. This festive affair includes a Handmade Holiday Market, a visit from Santa Claus, and a massive race in which a bunch of Santa clones charge down Main Street in the name of charity. The annual Dew Tour is next up on the calendar, just a few weeks later, in which snowboarders and skiers compete in Olympic qualifying events. The shredding is unreal, as competitors show off their skills on the halfpipe and slopes. Pick which athletes you think will make it all the way!

Though December is an incredible time to experience Breckenridge, stick around for January, so that you don’t miss out on some of the city’s most popular festivities. For 55 years running, Ullr Festival has hosted a massive party in the name of the winter god, Ullr, and there’s no better way to celebrate than with Viking attire, parades, ski jumps, and the biggest bonfire you’ve ever seen. And if that wasn’t rad enough, the Breckenridge International Snow Sculpture Championships continues the frigid fun with the most impressive snow creations along Riverwalk Centre—it takes the artists five days to craft their icy masterpieces! Sounds like you’ll have to clear your calendar for two incredible months in Breckenridge so you don’t miss a beat.

Bloomington, IN

Yes, Bloomington wears winter beautifully with its snow-draped scenery, but it’s autumn that captures the hearts of visitors and locals alike. September, in particular, is when you’ll find yourself wishing you had a body double so you could attend all the Bloomington activities!

This September, the annual Fourth Street Festival and Bloomington GarlicFEST & Community Art Fair competed for attention during Labor Day weekend. Fortunately, your FOMO wouldn’t run too wild though, as they set up just two blocks apart, giving you a two-for-one opportunity. Each year, the Fourth Street event features live music and spoken world, while the GarlicFEST presents, well, garlic-infused food, but also cooking contests, music performances, art displays, and more.

The seduction doesn’t stop there though; September also sees the Kiwanis Club of South Central Indiana Hot Air Balloon Fest and the Lotus World Music and Arts Festival. In the beginning of the month, colorful, patterned balloons linger along the horizon. At the annual Hot Air Balloon Fest, you can take a tethered balloon ride or admire the Balloon Glow with your feet on solid ground. Meanwhile, the Lotus festival closes out the month with culturally diverse art and music presentations. If you’re a local, you just may be able to pack it all in, but if you’re visiting, you may always wonder what you missed out on…

Jackson Hole, WY

Jackson Hole and all of its surrounding rugged beauty make it tough to decide when to visit, but add in all of the top-notch events, and you’ll find yourself torn: springtime festivities or frosty winter contests?

The end of May brings with it the start of wildflower season and the much-anticipated Elkfest, a 50-year-old local custom in which the Jackson Hole Boy Scouts and U.S. Fish and Wildlife collect shed elk antlers and auction them off in Town Square. Traditionally, Elkfest kicks off Old West Days, which takes place over Memorial Day weekend. Old West Days celebrates the region’s heritage with events, such as Mountain Man Rendezvous and Traders’ Row, Old West Brew Fest, and the Jackson Hole Shootout. You’ll even get your chance to see the first rodeo of the season!

Fast forward a few months and several snow storms later, and you’ll discover the allure of Jackson Hole winters. Not only are the slopes at Snow King Mountain and Jackson Hole Mountain Resort open for shredding, but late January brings with it the International Pedigree Stage Stop Sled Dog Race. Seeing the mushers and huskies in action is an epic bucket-list event, but if you were to stick around for February, you’d see the snow sport action at the Annual Moose Chase and Dick’s Ditch Classic Banked Slalom. So, what’s it going to be?

Tucson, AZ

Not too hot and not too cold, Tucson is the Goldilocks of winter destinations, making January a prime time to explore this dramatically scenic Arizona city. And it’s not just the temperatures that make Tucson so appealing during winter; the city hosts countless artsy January events to trigger your FOMO.

Do you hear that? It’s music—music coming from every corner. In the middle of January, Tucson Jazz Festival turns up the volume for 11 straight days, with musical acts performing at venues all over town, including the free all-day Downtown Jazz Fiesta. Overlapping with the jazz ensembles, the Tucson Desert Song Festival runs for three weekends, showcasing soloists with renowned Arizona groups, such as the Tucson Symphony Orchestra and the Arizona Opera. That’s music to your ears.

Feeling the pressure yet? Well, it gets worse: the Tucson Fringe Theater Festival (a 3-day presentation of avant-garde art performances) and the Tucson International Jewish Film Festival run at the same time during the middle of January. And just to further up the ante, the world’s largest gem show, the Tucson Gem, Mineral & Fossil Showcase sets up shop at the end of the month. Sorry, not sorry!

Rockland, ME

It’s always a good time to visit Rockland, but the seaside city really takes it up a notch come summertime. So much so, you’ll find yourself pressed to decide which events and attractions to put at the top of your list. The much-celebrated events are a must, but don’t overlook an afternoon strolling Main Street and a sailing adventure on Penobscot Bay.

July in Rockland is responsible for all your FOMO fretting, as it kicks off the fun with the Maine Windjammer Parade. You’ll soon realize the significance of maritime ways on this stretch of coastline, as the annual windjammer procession celebrates its nautical roots with a fleet that sails past Rockland Breakwater. For more seafaring celebrations, you can’t skip Friendship Sloop Days, which commemorate the Friendship sloop design.

Amid all the sailing jubilees, the North Atlantic Blues Festivals wails. This 2-day musical frenzy, puts the spotlight on some of the East Coast’s finest blues musicians—something you’ll totally regret not experiencing for yourself. While the blues fest hits the Public Landing stage in middle of the July, the incredible Maine Lobster Festival doesn’t occur until the first week of August, which means you’ll have to either stay in town or make a choice. Did we mention that they serve more than 20,000 pounds of locally caught lobster during the famous foodie fest? Yeah, good luck choosing.

Bethlehem, PA

You’ve heard all about Christmas City and you’ve been planning to see the holiday cheer for yourself, but did you know Bethlehem has its fair share of summer shindigs, too? The FOMO struggle is real in this PA town, where you’ll have to pick between warm outdoorsy events and the magical holiday festivities.

When it comes to the summertime, even deciding between July and August will be tricky, as late July brings the annual Blueberry Festival, while August welcomes both the Musikfest and VegFest. Celebrating all things blueberry, the July festival is a fruit lover’s dream with cook-offs and eating contests, while the VegFest sets up in late August, serving up the finest vegan eats in the Lehigh Valley. As for the Musikfest, this 10-day music extravaganza makes some noise as more than 300 performers take the stage.

Come wintertime, the Christmas spirit starts as early as mid-November, as Bethlehem ramps up the annual Christkindlmarkt, a 5-week bazaar. Representing its biblical namesake, the city delights with other holiday-themed events, including a Live Advent Calendar, Christmas City Stroll, and a Bethlehem By Night bus tour. Sounds like a prime time to crack open the eggnog!

Madison, WI

If you’re exploring Madison in July, you’re in for a doozy. Your schedule will either be packed to the brim, or you may find yourself choosing between events (and having major FOMO as a result). But let’s be honest, having too many fun things to do in Madison has never been a bad thing!

The Art Fair on the Square is a 2-day event in July that shows off the wildly creative talent of more than 500 artists. Hosted by MMoCA, this art fest takes over Capitol Square with nearly every kind of art work you could imagine—sculptures, jewelry, photographs, prints, and more. To see more of what the locals have up their sleeves, you won’t want to forgo the Dane County Farmers Market, every Wednesday and Saturday, which is the nation’s largest producer-only market.

The incentives keep on coming though, as the Dane County Fair sets up shop for five days in July, bringing with it carnival rides, nightly concerts, and stunt shows. And if that wasn’t appealing enough, the Wisconsin Chamber Orchestra presents Concerts on the Square every Wednesday night from June to July; a real musical treat. Can you fit it all in?

Ocean City, MD

Here’s the thing, Ocean City in the summertime is something you need to experience at least once in your life: splashing in the Atlantic to cool off, eating an ice cream cone on the boardwalk, and getting dizzy on the rides at Jolly Roger. But the beauty of this coastal town is the fun doesn’t stop when the tourist crowds leave after Labor Day. In fact, September is just when the party’s getting started! So, the predicament lies in whether you stick around for the summertime vibes or linger in early autumn when the calendar is crammed full.

In the middle of September, you can pretend summer is still going strong at the annual Sunfest, a free multi-day event with live music, crafts, and good eats, or you could don your favorite leather jacket and join 150,000 bikers at the legendary Bike Week. Better yet, Wine on the Beach occurs at the end of the month, inviting you to sip grape libations right on the water,

But you if you stick around for the first weekend of October, you’ll thank yourself later. The engines start revving at Endless Summer Cruisin’, a massive vintage car show with everything from hot rods to tricked-out trucks. There are a ton of must-attend events during this time, if you don’t make time to soak up those last remaining beach days, before the chillier temperatures arrive, you just may regret it later.

Las Cruces, NM

Las Cruces, with its scenic mountain backdrop, belongs at the top of your list. Beyond its beauty, it hosts a myriad of events throughout the year that will make your friends jealous—and you, if you don’t experience them all to the fullest. September is an especially happenin’ time in town as the state’s second largest city ramps up its calendar with all kinds of super cool fests. You’ll be green with envy if you miss any of these attractions:

Grape stomping and wine tasting jumpstart the month of September in Las Cruces—does it get much better than that? The New Mexico Wine Harvest Festival is a 3-day revelry of the grape variety, with live bands and glasses filled high with juice from the local wineries. That’s just the start of the excitement though, as the Southern New Mexico State Fair & Rodeo rolls into town toward the end of the month, complete with bull rides, livestock shows, stunt performers, and petting zoos. Competing for your attention, the Mesilla Valley Maze sets up at the end of September through October, where you’ll get lost in the 5-acre corn maze and spend all day roaming the 20+-acre pumpkin patch to get you in the Halloween state of mind.

The awesomeness extends beyond the city limits, as neighboring Old Mesilla and Hatch have their own enchanting events that will further put you in a predicament. Do you stick in town for Las Cruces’ rodeo or do you venture to Old Mesilla for the Diez y Seis de Septiembre Fiesta for mariachi music and Mexican comida? We hate to break it you, but nearby Hatch holds the Hatch Chile Festival in September, too, where you can devour the famous pepper in what is considered the chili capital of the world! We can already feel the FOMO kicking in…

Huntington Beach, CA

No matter what time of year it is, Huntington Beach has got it goin’ on. Both long and short boarders flock to Surf City USA to ride the waves all year long, but even if you fancy yourself more a landlubber, you’ll soon realize this seaside city is where it’s at. Late May and into June (ok, even July!) is when you’ll really see the city’s flair, and that means deciding between all the tempting attractions.

Toward the end of May, you could spend all day basking along the beach town’s picturesque shoreline, or you could attend the annual Duck-A-Thon. Raising money for the AltaMed’s Huntington Beach Community Clinic, this quirky event’s highlight is the rubber ducky race, where 4,000 plastic duckies race to shore. Along with the yellow ducky theme, the 3-day affair includes wine tasting, food vendors, arts, crafts, and tons more attractions.

As May turns to June, there’s even more temptation on the horizon. The Huntington Beach Pier Swim is celebrating its 68th year in 2018, as teams of swimmers dash into the water and swim the half-mile course around the Huntington Beach Pier in hopes of winning the Gene Belshe Memorial Perpetual Trophy. Around the same time, the Huntington Beach Concours d’Elegance is an automobile lover’s dream, as vintage cars and brand-new whips sparkle on the grass of Huntington Beach Central Park. You probably don’t want to hear it, but the largest parade west of the Mississippi River occurs in the coastal city during the Fourth of July, and the US Open of Surfing takes over the beach at the end of July. Come fall, the Breitling Huntington Beach Airshow in October draws crowds to witness demonstrations by top air squadrons…will you ever forgive yourself if you skip out?

Bardstown, KY

Any time you explore the wonderful world of Bardstown, you have to consciously keep your FOMO in check, but visit during the fall, and you’ll find yourself in a whole other ball game. Everyone clears their schedules for the annual Kentucky Bourbon Festival, but trust us, that’s not the only thing to catch your fancy in this part of town!

In early September, the Kentucky Bourbon Festival invites you to sample “the world’s finest spirits in the Bourbon Capital of the World,” and we can’t argue with that! For seven straight days, the bourbon is flowing, but in addition to tastings, they put on all kinds of events from spectacular galas to photography contests. Not to stray too far from the city’s whiskey ways, give into temptation as you experience the Barton 1792 Distillery Sundown Series for more bourbon tastings, food truck fare, and live music.

After all those shots, it’s time for some suds at the Bardstown Craft Beer Festival! This October brew bash pours more than 30 local and imported beers and serves local cuisine, giving you a sweet taste of the region’s flavor. But you better believe that’s not the only alluring entertainment on the schedule. October weekends at FFA Field of Terror Haunted Corn Maze will test your bravery, while the Bardstown Arts, Crafts, and Antiques Fair showcases more than 200 booths with wares from local vendors. So much to do, so little time!

What cities give you the worst case of FOMO?

Photo attributions:

Top Left: Flickr/City of Boston Archives
Top Middle: Flickr/Jeff Gunn
Top Right: Flickr/Madeleine Ball
Bottom Left: Flickr/JD
Bottom Right: Flickr/Ken Lund

San Diego
Top Left: Flickr/Heng Ung
Top Right: Flickr/Steve Dolan
Bottom Left: Flickr/Kevin Dooley
Bottom Middle: Flickr/Port of San Diego
Bottom Right: Flickr/Steve Dolan

Little Rock
Top Right: Yelp/Jefferey A.
Bottom Left: Yelp/C D.
Bottom Right: Yelp/Noah H.

Top Left: Yelp/Dan V.
Top Middle: Flickr/Brian Wibbenmeyer
Top Right: Flickr/Tydence Davis
Bottom Right: Flickr/Thaddeus Roan

Left Top: Flickr/Jeff Hart

Jackson Hole
Left Top: Flickr/Larry Johnson
Left Bottom: Flickr/xcDogs LLC
Right Top: Flickr/Dion Hinchcliffe
Right Middle: Yelp/Kristie J.
Right Bottom: Flickr/Chuck Grimmett

Left: Yelp/Kamryn C.
Right Bottom: Yelp/Angela W.

Top Right: Yelp/Danielle F.
Bottom Left: Flickr/Rebecca Siegel
Bottom Middle: Flickr/madamjujujive
Bottom Right: Flickr/kmf164

Top: Flickr/Bill Dickinson
Bottom Far Left: Flickr/Lehigh Valley, PA
Bottom Middle Left: Flickr/Jack
Bottom Middle Right: Flickr/Lehigh Valley, PA
Bottom Far Right: Flickr/Mike Rastiello

Bottom Left: Yelp/Samantha H.
Bottom Middle: Yelp/D. M.
Right: Yelp/John P.

Ocean City
Top Left: Flickr/John M.
Bottom Left: Flickr/Lee Cannon
Right: Flickr/m01229

Las Cruces
Top Left: Flickr/Nan Palmero
Top Right: Flickr/Stuart Seeger
Bottom Left: Yelp/Brieanna W.
Bottom Right: Yelp/David T.

Huntington Beach
Top Right: Yelp/Emma J.
Bottom Left: Flickr/YoTuT
Bottom Middle: Flickr/Rian Castillo
Bottom Right: Flickr/ksablan

Top Left: Yelp/Duke Of Frisco X.
Bottom Left: Yelp/Dwayne S.

Expedia compensates authors for their writings appearing on this site, such compensation may include travel and other costs.

Chloe Mulliner

As a staff writer for Expedia, Chloe Mulliner is dedicated to providing top travel tips for your jaunts around the world. She believes there are adventures to be had on every inch of the globe from surf spots on the Peruvian coast to the charming villages of the English countryside. Chloe specializes in showcasing all the must-see attractions on your travel wish list. She lives by the belief that every adventure is a story worth sharing.

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