10 Best Destinations for an Autumn Break

Boston is a fascinating place at any time of the year, but the leafy city really shines as summer fades into fall. With the leaves changing to a riot of colours, the city’s parks become fantastic places to enjoy the outdoors. Among the many beautiful spots to explore at this time of year are the Rose Kennedy Greenway, Boston Common, and the Charles River Esplanade.

Naturally, there’s more to Boston in fall than just colourful leaves. You can expect fun festivals like Oktoberfest and the Charles Regatta, not forgetting Halloween celebrated in nearby Salem – a month-long celebration thanks to the town’s notorious history with the supernatural.

Miami is a fantastic place to go for a fall break, especially if you’re not quite ready for summer to end. Florida’s tropical climate ensures that you can still enjoy beach weather. Indeed, autumn marks the point at which the weather drops down into the more comfortable, sub-90°F range.

The city takes full advantage of these more pleasant conditions, with fall bringing extra musical concerts, Miami Carnival, the South Beach Seafood Festival, and the HalloWYN Wynwood Halloween Block Party. You probably won’t see many changing leaves, so your break might not feel especially autumnal. However, it’ll certainly make an entertaining holiday.

Leafy Washington, DC has plenty of great places to see vibrant displays of red, orange, and brown fall foliage, as well as exciting events and festivals at this time of year. The National Mall, National Arboretum, and the Tidal Basin, are just 3 of the many iconic spots in the capital that are decorated with nature's autumnal colours.  

Once you’ve ticked leaf peeping off your list, you now have Washington’s various autumn festivals to check out. Oktoberfest, the Georgetown French Market, music concerts, and sports events await. This is also a great time to visit the most popular of DC’s attractions, too, as the summer crowds start to ebb away.

Chicago is famous for its food and the fall season marks a high point in the culinary calendar. You can expect pies aplenty, with pumpkin, pecan and sweet potato pies being prepared for the upcoming Thanksgiving Holiday. There’s also Oktoberfest’s beer and Halloween’s sweets to look forward to. Look out for food festivals like Chicago Gourmet and the Harvest Wine & Cheese Festa, too.

Being in the northern, temperate part of the US, Chicago is naturally a fantastic place to see the changing fall foliage, with Lincoln Park, Jackson Park, and Morton Arboretum all excellent spots to do so. Autumn also brings special art events, including museum and gallery exhibitions and premiers of new theatre shows.

Key West, like the rest of Florida, doesn’t experience fall in the same way as the rest of the US. The weather just gets slightly less hot and sunny, and the seas get a little bit cooler. If you’re looking for a last little dose of summer warmth before winter sets in, this delightful little island will serve you well.

Leaf peepers won’t have much to see in Key West as the tropical plants don’t change colour. By contrast, wildlife spotters have plenty to see. Migrating bird species can be seen passing through, especially in the Key West Wildlife Refuge and Florida Keys National Maritime Sanctuary. There are also plenty of fishing and dolphin-spotting tours to enjoy at this time of year.

Gatlinburg and Pigeon Forge provide a double-whammy of entertainment during fall, offering the opportunity to enjoy very different types of holiday in a relatively small space. Gatlinburg is particularly popular, being the gateway to one of the nation’s most popular national parks – the Great Smoky Mountains. Taking a scenic drive or hike through the beautifully colourful scenery is a must.

Head a little north to Pigeon Forge and there are the many family-friendly attractions that you can access throughout the year, as well as the delightful flavours of the harvest. Think wines, toffee apples, ciders, and moonshine. There are plenty of fun festivals in the area at this time of year, too.

The area of St Petersburg and Clearwater provides the fantastic weather and beaches of many great Florida destinations, with the added advantage of being a large and cosmopolitan city. Even in fall, with temperatures dropping only slightly, this remains a fantastic destination for a beach break.

Autumn presents wonderful festivals in St Petersburg and Clearwater. The main one is simply called the Autumn Festival – a fun and festival community event that brings entertainment for all ages. There’s also the Sanding Ovations Master's Cup showcasing the work of expert sandcastle builders, the Clearwater Jazz Holiday, as well as various variants of the iconic autumn festivities like Oktoberfest and Halloween. You’ll have plenty of opportunities to get out and enjoy the lovely weather.

Autumn is arguably the best time of year to visit San Francisco. Unusually, it offers some of the best, warmest temperatures, combined with fewer crowds around the top attractions. The city’s famous fog starts to recede after August, too, so you can even enjoy the views properly.

Of course, there’s more to San Francisco in fall than just warm weather and fewer people. Fleet Week is well worth seeing, as is the Castro Street Fair and Chinatown Autumn Moon Festival. And that’s barely scraping the surface of the many outstanding events to enjoy at this time of year.

Paris is well worth a visit at any time of the year, but fall is a fantastic time for photographing the City of Lights. The leafy city becomes an explosion of autumnal colours, giving the famously romantic destination a last big show before the winter, especially in the beautiful parks and along the River Seine.

It’s not just the leaves putting on a show, either. Autumn is culinary season in Paris, so expect some tasty treats to come out of the wine harvest and food markets. There’s even a wine harvest festival in Montmartre and many more in nearby wine regions. The city’s main attractions also see smaller crowds, so it’s a great time to see the most popular sights, too.

London really cranks up the festive atmosphere in fall. The most iconic is the famous Bonfire Night on November 5^th, but others include the London Cocktail Week, the BFI London Film Festival, EFG London Jazz Festival and, of course, Halloween.

With its large royal parks, commons and other green spaces, London becomes a riot of colour during fall. Be sure to check out Richmond Park to see the deer, the wild Hampstead Heath and, for a change, Kyoto Garden in Holland Park.