High Times at Fall Beer and Wine Festivals - My Family Travels

Fall for fun beer and wine festivals with their many free outdoor activities this season. Despite the resurgence of the pandemic, there are many options for adult getaways, whether you’re BFFs or couples. Most events accommodate all guests, even if you have the kids in tow.

Fall & Oktoberfests in NY State for Good Times

Enjoying the local craft brews at Hunter Mountain’s four weekends of Oktoberfest. Photo c. Hunter Mountain.

Head to upstate New York for a wide variety of peak seasonal gatherings. (And we don’t mean the departure of the governor.) The changing leaves are the focus of the 90-minute Dutch Apple sightseeing river cruises, with itineraries on the Hudson or through the Erie Canal locks in Troy.

Visit Sept. 25 and 26 for the first weekend of Hunter Mountain Oktoberfest which features a “Ciders in the Catskills” tasting. The following three weekends are themed to the season: in October go off-roading in the Catskill Mountains to see the leaves change. The Das Laufwerk Eurocar Rally speeds into town the third weekend of the month, followed by a program of fall activities and wine tastings at month’s end.

For a sky-high view while you’re there, book the New York Zipline Adventure Tour at Hunter Mountain. It’s the highest, fastest, and longest zipline canopy tour in North America and — they like to say — the second largest zipline in the world. Don’t start worrying yet, there are three levels of challenge for all ages.

Sky High over Fall Foliage

Gallup, New Mexico and the surrounding Native American lands seen from a hot air balloon
Enjoy the New Mexico landscape and surrounding Native American lands from a hot air balloon. Photo c. GallupNM.gov

Autumn seems to make balloons fly higher. Snowmass, Colorado will send three dozen colorful hot air balloons soaring over this ski town and down the Roaring Fork Valley from September 10-12 during the Snowmass Balloon Festival.

The Dallas suburb of Plano, which has grown fast thanks to the influx of large corporations and the many young families who follow them, is hosting the Plano Balloon Festival September 17-19, 2021. It features rides in a tethered balloon (ages 6+) that hovers for several minutes over the festival grounds. Don’t miss the popular Balloon Glow at sundown, when the rigs’ flames illuminate the sky.

The grandmother of all sky-high festivals is the Albuquerque Balloon Fiesta in New Mexico, held this year from October 5-13. Mass Ascension, a launch of all the participating balloons has been a feature of Balloon Fiesta since its earliest days and is a spectacular display of sound and color. It will take place on October 2-10, 2021 starting at 7:00am on each day. Be sure to check out other great fall getaways if you’re traveling with younger ones.

Celebrate So Much More than the Harvest

It’s the best time of year if you’re Scottish at the annual Ren Fair in Wichita, Kansas.

The Great Plains Renaissance Festival will take place in Wichita, Kansas from September 25-26, a time when knights, knaves and fairies educate the crowds about life in medieval times. Take a swig of their local brews while enjoying the many performing artists, costumed re-enactors and tasty treats. Stick around and participate in the annual Wagonmasters Chili Cookoff, which has brought 80 Midwest teams and thousands of spectators to eat, chill out and watch the crowning of Mr. Hot Stuff and Ms. Chili Pepper for more than 30 years. 

Due north and east, the 15th annual North American Wife Carrying Championship (October 9) pits couples against each other on a 278-yard obstacle filled track at Sunday River Maine’s Fall Festival. Of course, there’s plenty on draft to follow up this competition which puts a strain on as many backs as marriages.

Do you prefer Salted Chocolate Fudge or the boozy Bourbon Pecan? It’s never too cold for all-natural Velvet Ice Cream in Utica, Ohio, where family owners have been celebrating its success for the past century. This fall is no different; there are snacks, cones and full meals at Ye Olde Mill, the company’s HQ is a historic, riverfront mill. Open Tuesday to Sunday, lunch and dinner.

Pirates Take You Higher

The Pooch Parade takes place during Cayman Islands’ Pirate’s Week. Photo c. Taneros Ramsay

Yes, autumn is the time for beer and wine festivals but they’re much more fun if pirates and music are involved. Each November, for three long weekends (Nov. 6-21, 2021), the beautiful Cayman Islands holds Pirate’s Week. Picture those booze cruises on dramatic looking replica schooners, add in live music, a bit of Johnny Depp, Mardi Gras style costumes, parades, fireworks… and you get the basic vibe. People go to the Caymans for Pirate’s Week to have fun.

Book your lodgings way ahead of time and plan to be on the right island (events take place on Grand Cayman, Little Cayman and Cayman Brac) for your preferred events.

William Cepeda performs at the Dominican Republic Jazz Festival
William Cepeda performs at the Dominican Republic Jazz Festival; photo by Gabriel Rodes.

For nearly 25 autumns, the Dominican Republic Jazz Festival has been presented by FEDUJAZZ and the Ministry of Tourism. The festival’s acclaimed lineup has included favorites such as Esperanza Spalding, Chucho Valdés and Chuck Mangione. Shows are free, with VIP tickets sales benefitting FEDUJAZZ, which provides free music education for the youth of the Dominican Republic. Book hotels early for this one.

Having staged only one concert in the Covid-era, they hope to return in person for 10 days of events in Fall 2022. Past shows took place in Cap Cana, Santiago, Centro Leon and Cabarete Beach, the country’s windsurfing capital and home to the FEDUJAZZ foundation.

Drink to the Harvest

Wine and glass
Sample and sip to your heart’s content in Sonoma.

And what about the season’s beer and wine festivals? Hope you’re sitting down!

The Munich Oktoberfest has been postponed for the second time in a row. The annual Sonoma County Harvest Fair will not be held this year, either, though they hope to reappear in early October of 2021. Put it on your bucket list for the lavish program of wine and microbrew tastings, plus the chance to join the World Championship Grape Stomp. And if you’re ready to harvest personal fitness – even if you have to borrow gear or rent it from REI – explore California’s Wine Country on foot or mountain bikes at its most beautiful time of year.

Vail Mountain celebrates its fall Oktoberfest over two weekends in September, with many family events scheduled in the base villages. The dates for the Lionshead village are Sept. 6-8 and, in Vail Village, Sept. 13-15, 2021.

If you feel like you’re missing Oktoberfest, several destinations celebrate craft brews and spirits all fall. The 39th annual New Ulm in Minnesota, which will take place on the first two October weekends in several venues, will feature both local brews and wines.

The First Hops Festival is the centerpiece of the Sugarbush Resort Community Weekend (Oct. 10) in Warren, Vermont. Meet the 10 Vermont breweries who are producing fresh hopped beer, which is only brewed during the early autumn harvesting season because it has a very short shelf life. Organizers say that beers brewed with fresh hops tend to have a distinctively “green” flavor profile, without the classic bitterness that more hoppy beers like an IPA often have.

Kids and pets are usually welcome in Breckenridge, Colorado, but you’ll want to leave them behind for the popular Craft Spirits Festival Oct. 8-10, 2021. A tip from Breck locals: Relax and save big time on restaurants with early Happy Hour menus.

Yay Happy Hour! Let’s toast our favorite fall events and beer and wine festivals!

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