5 great fall destinations, and how to fly there nearly for free

Use points to get to Disneyland and other great places this autumn

Lyn Mettler
Personal finance writer
Specializes in writing on travel, family and food

5 great fall destinations, and how to fly there for free

Fall is my favorite time of year. I love the changing leaves, the cool weather and Halloween, and my family finds it to be a great time to travel. 

There are usually cheap prices for flights, and destinations usually aren't too crowded during fall school breaks. Here are some of our top places to visit in the fall, and how we get there nearly for free.

1. California’s wine country

Did you know the grapevines in California’s wine country turn splendid colors of red, orange and gold each fall? It's a great time to sample wine and explore the fantastic outdoors in Sonoma County and the Napa Valley.

One of the best ways to see it is with Sonoma on a Bike, which offers six-day bike tours of area wineries, replete with accommodations and meals at some of wine country’s finest establishments. We also loved taking a hot air balloon flight over the Napa Valley with Napa Valley Balloons. We could literally see all the way to San Francisco!

We’ve also kayaked through redwoods on the Russian River and hiked the beautiful Sonoma coast with Getaway Adventures, which offers day kayaking, biking and hiking tours throughout the region. 

You can fly most cheaply on Southwest Airlines into San Francisco, Oakland or San Jose. You can also fly directly into Santa Rosa – the largest city in the wine country area – via American Airlines. Santa Rosa is frequently one of the airline’s Reduced Mileage Awards destinations that save holders of select AAdvantage credit cards up to 7,500 miles round-trip.

2. Telluride, Colorado

One of my favorite spots in the world is the Rocky Mountains of Colorado, and one of the most spectacular hidden gems we’ve ever come across is Telluride. This gorgeous Wild West town, founded during the gold mining era in the late 1800s, is set in a box canyon and surrounded by the San Juan portion of the Rockies. 

One of the most scenic freebies in the country is the gondola ride from the Mountain Village ski area down into town, particularly when the aspens turn gold in the fall. There is also plentiful hiking in Telluride right from town, as well as mountain biking, off-roading, fishing and all manner of outdoor activities. The Hotel Telluride is a comfy spot that offers free shuttles throughout the area.

To get to Telluride for free, consider flying American Airlines into Montrose, Colorado, which is about 65 miles away and is also frequently part of the Reduced Mileage Awards program. Alternately, you can book an awards flight from Chicago on United Airlines. The route we take is to fly Southwest to Denver using our Rapid Rewards points, and then make the 300-plus-mile drive to Telluride in a rental car. Part of the town's charm is that it’s not easy to get to.  

See related: Travel rewards: Use your hobbies to earn miles, points 

3. Disneyland

Have you ever been to Disneyland at Halloween? If not, add it to your list! 

Not only is the park totally decorated for the holiday, the Haunted Mansion ride gets a complete “The Nightmare Before Christmas” theme, and a haunting film plays during the ride at Space Mountain. There’s also a special fireworks show and an awesome Halloween parade. It’s perfect for all ages (my kids were 9 and 13 at the time we went).

There are only a handful of Disneyland resorts, but they tend to fill fast. We chose to stay at the Hilton Anaheim and the Anaheim Marriott – each one is a quick Uber ride from the parks.

We took our family last Halloween using Southwest points to fly from Indianapolis to Los Angeles International Airport, and then made the short drive to Disneyland in Anaheim.

4. New York City

The autumn is my favorite time to visit the “City That Never Sleeps.” I just love the foliage in Central Park, the crisp weather and the chance to see live TV shows as they start back up for the fall season. 

We like to stay in hotels in the quieter areas of town, such as the Hotel Elysee in Midtown East or in Brooklyn at The Williamsburg Hotel. The trendy meatpacking district is also fun, with options such as the Gansevoort boutique hotel.

There’s never a shortage of activities in New York City. I recommend catching a comedy act at the Comedy Cellar (we were surprised to have Aziz Ansari take the stage unannounced during our last stop), eating at local-favorite Joe’s Pizza and taking a stroll down the High Line in Chelsea. 

Be sure to get out on the water, too. Cheap ways to do that include the New York City Ferry from Brooklyn and a ride on the Staten Island Ferry, from which you can see the Statue of Liberty.

It’s nearly always cheap to fly to New York City on points via Southwest, which is how we typically reach the Big Apple.

See related: Multi-attraction passes help you save on big city travel 

5. Paris

After we visited Paris in 2017, it quickly became my favorite city in the world. To me, its architectural beauty is unparalleled. 

Fall is a great time to see the City of Light, as the weather is mild, the summer crowds are gone and the greenery at its many parks turn fantastic colors.

For a great guided tour company, check out The Paris Guy, which offers tours to the Catacombs (which can be nearly impossible to do on your own due to long lines), Versailles and the Louvre. Another tip for visiting the Louvre is to go on a Friday night when it stays open later and the crowds are thin. Additionally, the Paris Opera House is often overlooked, but its lavish décor is jaw-dropping. 

The city is extremely walkable, so it’s cheap to get out and explore, while allowing time to stop for a baguette and rest along the Seine. We enjoyed staying at both a Left Bank apartment that we booked through HomeAway, as well as the Hotel Indigo Paris Opera, which is convenient to everything on the Right Bank and located in a charming hidden alcove off a main road.

To get to Paris, we took advantage of Aer Lingus’ off peak dates, which allow you to fly from major U.S. cities like New York and Chicago to Dublin for 26,000 points round trip per person. We used additional Aer Lingus Avios to fly from Dublin to Paris, but you could also opt to fly on an inexpensive airline like Ryanair. 


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Updated: 11-19-2018