Next, drive about 15 miles north to Niagara-on-the-Lake, a quaint 19th-century village in Ontario’s wine country. Each September, the town hosts its annual 2 1/2-week Niagara Grape & Wine Festival, featuring local food vendors and more than 100 events, including cellar door experiences, wine tastings, parades and concerts. In town, explore local 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.
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, which divides the U.S. and Canada, winds drivers along the Niagara River and offers spectacular views of fall colors during late September and early October.
Also Consider: Portland, Maine
- Average daily temperatures in September range from 50 to 70 degrees Fahrenheit.
Leaf peepers need only drive about 20 miles northeast from Portland to reach Bradbury Mountain State Park, frequently noted as one of the best places to see fall colors. By September, 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, the Portland area hosts several fall festivals, from Family Harvest Days to Ales for Tails. September visitors can also stop by one of Portland’s many brewpubs, like local favorite Bissell Brothers. Sample seasonals such as its Baby Genius, a hoppy session beer available through early October, or year-round, rotating pours such as its Bucolia amber ale.
Best Places to Travel in October
Top Recommendation: Chicago, Illinois
- Average daily temperatures in October range from 42 to 62 degrees
Chicago takes full advantage of October’s pleasant weather as scarves come out, autumnal colors burst and pumpkin patches pop up, such as Sonny Acres in West Chicago. The city hosts more events than you could possibly choose from in October, such as the Chicago International Film Festival, 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. Or 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 and features more than 50 Midwest beers and dozens of bacon-infused dishes.