Next, drive about 15 miles north to Niagara-on-the-Lake, a quaint 19th-century village in Ontario’s wine country. In town, explore wineries, go antiquing and stay at The Butler House, a romantic bed-and-breakfast dating back to the late 1780s. The house was thought to have been used as a secret militia meeting place by Col. John Butler and Butler’s Rangers, a loyalist regiment fighting for Britain during the American Revolution.
Each September, Niagara-on-the-Lake and its neighboring towns, St. Catharines and Twenty Valley, host the weekslong Niagara Grape & Wine Festival. Choose your own adventure with a Discovery Pass, which grants access to more than 30 wineries in Niagara-on-the-Lake and Twenty Valley during all three weekends of the event. Or enjoy more than 100 wines, 50 hours of live music and VIP lounges in downtown St. Catharines’ historic Montebello Park during the second and third weekends of the fest.
Insider Tip: Make time for an afternoon cruise down Niagara Parkway for what Winston Churchill described as “the prettiest Sunday afternoon drive in the world.” Easily accessible from Niagara-on-the-Lake, this Ontario parkway winds drivers along the Niagara River on the U.S.-Canada border and offers spectacular views of fall colors during late September and early October.
Also Consider for a September Vacation: Portland, Maine
- Average daily temperatures in September range from 50 to 70 degrees.
Leaf peepers need only drive about 25 miles northeast from Portland International Jetport to reach Bradbury Mountain State Park, frequently noted as one of the best places to travel in September. By then, Portland’s peak summer tourism season has passed, which makes it less crowded and often less expensive to visit than in summer. Much like the rest of New England, Portland and its surrounding areas host several fall festivals and events. Enjoy barrel train rides and butter churning demonstrations at Family Harvest Days or pumpkin and squash weigh-off contests and harness racing at the Cumberland County Fair, just a 15-mile drive northwest of Portland. September visitors can also stop by one of Portland’s many brewpubs, like local favorite Bissell Brothers. Sample seasonal beers such as its Baby Genius, a hoppy session beer available through early October, or year-round rotating pours.
Best Place to Travel in October: Chicago, Illinois
- Average daily temperatures in October range from 46 to 64 degrees.
Drive 11 miles northeast from Chicago Midway International Airport or 18 miles southeast from Chicago O’Hare International Airport.
What to See and Do
During this time of year in the Windy City, scarves come out, autumnal colors burst and pumpkin patches, such as Sonny Acres in West Chicago, pop up in and around town. The city hosts more events than you could possibly choose from in October, including the Chicago International Film Festival, the Fall Bulb Festival and even a Halloween parade for dogs.
This time of year also beckons travelers to the Chicago Botanic Garden, where Japanese maples transform into shades of fiery red. Take a drive to Millennium Park to snap a family photo with the park’s beautiful foliage and the city’s skyline in the background. During your fall getaway, Lake Shore Drive will connect you to popular year-round Chicago attractions like Navy Pier, Shedd Aquarium and Soldier Field, which hosts the Chicago Bacon and Beer Classic every fall. At this event, sample more than 100 craft beers and dozens of bacon-infused dishes. Another must-see attraction is Chicago’s Magnificent Mile, which boasts more than 200 restaurants and 400 shops — making it easy to pick up a new seasonal accessory during your October vacation. Stay nearby at the Homewood Suites by Hilton Chicago-Downtown, where families can enjoy complimentary breakfast and Wi-Fi as well as a year-round indoor swimming pool.