As someone who lives in Texas, where fall feels like a distant, fictional concept rather than an actual season, I’ve always turned to certain movies to get into the autumn spirit. Namely: When Harry Met Sally, Sleepless in Seattle, and You’ve Got Mail. In my opinion, the patron saint of fall films is none other than Nora Ephron. Her rom-coms aren’t just the blueprint for my unrealistic romance expectations, but they perfectly encapsulate the cozy, warm energy I crave every year. While I’m usually content with my annual Nora Ephron triple feature movie marathon to signal the start of autumn, this year, I’m dreaming of taking it a step further—actually living the Nora Ephron fall fantasy with a trip.
In Ephron’s films, the settings are as much a character as the romantic leads. The picturesque backdrops in her movies create the perfect stage for love stories to unfold. She has a unique ability to take big cities and infuse them with the charm and warmth of a small town, and a Nora Ephron-inspired fall trip should replicate that energy. Here are 10 cozy fall destinations that feel like they could be straight out of one of her films.
1. Boston, Massachusetts
Boston has that signature Ephron je ne sais quoi and is also a fabulous destination to experience fall in all its glory. Walk along the Charles River Esplanade for fall foliage views, and explore the historic Beacon Hill neighborhood, which is full of quaint shops and beautiful architecture. The Public Garden is another must-see for stunning fall colors. While New York in the fall might make you want to buy a bouquet of freshly sharpened pencils, in Boston, you can channel that back-to-school energy with a tour of the Harvard campus. Once you’ve tired yourself out from sightseeing, end the day with a classic New England lobster roll at The Barking Crab.
Where to stay: Porter Square Hotel (from $146 a night), The Newbury Boston (from $353)
2. New York, New York
Experiencing New York City in the fall is the ultimate way to live out your Nora Ephron-inspired fall dreams. Slip into your chunkiest knit sweater, queue up a ’90s rom-com playlist, and get yourself ready for the quintessential fall day in NYC. Visit iconic locations from her movies, like Katz’s Deli (is there a more iconic scene than “I’ll have what she’s having?”), browse the shelves of Shakespeare and Co., and stroll through Central Park. Of course, lunch at the Central Park Boathouse is highly recommended. The Metropolitan Museum of Art is also worth a visit, and you’ll be especially reminded of Nora Ephron when you get to the Egyptian collection, which you may recognize from When Harry Met Sally. Leave plenty of time for aimless wandering, popping into coffee shops and boutiques, and pretending you’re living in your very own Nora Ephron movie.
Where to stay: The Empire Hotel (from $123 a night), Chambers (from $265)
3. Philadelphia, Pennsylvania
Philadelphia is one of those big cities that can easily feel like a small town if you’re in the right areas. For a Nora Ephron-inspired Philly itinerary, start your day with coffee at Elixr or La Colombe’s tasting room (Philadelphia is the birthplace of the La Colombe empire). Sip your drink in Rittenhouse Square, imagining your very own rom-com-level meet-cute. Don’t miss the city’s many historical landmarks, like Independence Hall, the Liberty Bell, and the Betsy Ross House. Philly cheesesteaks are also non-negotiable, and Jim’s South St. is the best place to grab one for lunch. Once you’re fueled up, finish your day with a walk through Fairmount Park for autumnal views and peaceful trails.
Where to stay: Cambria Hotel Philadelphia Downtown Center City (from $135 a night), Kimpton Hotel Monaco Philadelphia (from $161)
4. Seattle, Washington
Seattle is an obvious destination for a Nora Ephron-inspired fall, thanks to Sleepless in Seattle. Start at Pike Place Market, where you’ll recognize the scene where Sam introduces Jonah to Victoria. While there, enjoy a meal at Athenian Seafood Restaurant & Bar, a filming location that features a plaque marking where Tom Hanks sat. Afterward, head to nearby landmarks like the Space Needle or Olympic Sculpture Park, then warm up with a coffee from the Starbucks Reserve Roastery. For a quintessential fall experience, bike through Washington Park Arboretum, where the vibrant foliage perfectly captures Ephron’s romantic vision of the city. It’s easy to picture Annie and Sam in their fall coats, wandering through the park arm and arm when they return to Seattle after their fateful meeting at the Empire State Building.
Where to stay: Hotel Ändra Seattle (from $160 a night), Fairmont Olympic Hotel (from $217)
5. San Francisco, California
Nora Ephron may not have a film set in San Francisco, but it’s easy to imagine one. I can easily picture two of her characters exchanging witty banter while ambling through Golden Gate Park amidst the changing leaves, visiting the iconic Golden Gate Bridge, or riding a cable car together, all of which should be on your itinerary. To round out your stay in San Fran, head down to the Fisherman’s Wharf to indulge in some clam chowder for lunch. Then shop your way down Lombard Street or explore the vibrant Haight-Ashbury and Mission Districts.
Where to stay: The Marker Union Square (from $96 a night), Hotel Emblem (from $106)
6. Chicago, Illinois
None of Nora Ephron’s characters spend much time in Chicago, but it’s where we begin both Sleepless in Seattle and When Harry Met Sally—so it certainly deserves a spot on this list of Nora Ephron-inspired fall destinations. For a unique view of the city, hop on a boat for the architecture tour along the river, which highlights some of Chicago’s most iconic buildings. The Art Institute of Chicago is another must-see, offering an incredible collection of artwork to get lost in. And don’t forget to visit the lively Navy Pier, which offers stunning lake views and plenty of things to do. When it comes to dining, Chicago has an endless selection of top-tier restaurants, but no visit is complete without indulging in the city’s most famous delicacy: deep-dish pizza. The local favorite Lou Malnati’s is a great place to grab a slice.
Where to stay: Pendry Chicago (from $156 a night), The Hoxton, Chicago (from $207)
7. Portland, Oregon
Portland experiences a stunning fall, with vibrant leaves and mild temperatures, and it’s easy to imagine a Nora Ephron-esque love story unfolding in this unique city. Since Portland is a major coffee destination, start your day at Stumptown Coffee, one of Portland’s most iconic cafes. Nora Ephron’s characters have a soft spot for independent bookstores (it’s literally the plot of You’ve Got Mail), and you just know Kathleen Kelly would be a fan of Powell’s City of Books—the largest independent bookstore in the world. After scooping up some literary treasures, make your way to Northwest Portland, where the tree-lined streets are sprinkled with shops and restaurants. Or head to Forest Park, one of the largest urban forests in the U.S., with trails that offer beautiful fall foliage views. To experience Portland’s signature quirkiness, spend an afternoon wandering around the Alberta Arts District, Mississippi Avenue, or the Hawthorne District.
Where to stay: Hotel Lucia (from $90 a night), Sentinel (from $96)
8. Baltimore, Maryland
While the plot of Sleepless in Seattle revolves around willing Annie to go to Seattle to meet Sam, she is in Baltimore for most of the film. The city is stunning in the fall, and you can definitely feel the Meg Ryan energy in the air. Start your day in the historic city center of Mount Vernon, one of the oldest neighborhoods in Baltimore and home to the original Washington Monument. You could easily spend the entire day exploring the museums, shops, and eateries this area has to offer. When you’re ready for a change of scenery, head to the Federal Hill neighborhood, known for its cobblestone streets, centuries-old row houses, and locally-owned shops and restaurants. Or wander around Hampden, where you’ll find tons of bookstores, art shops, and vintage stores. It’s the perfect place to discover some ’90s Ephron-inspired finds.
Where to stay: Hotel Revival (from $102 a night), Canopy by Hilton Baltimore Harbor Point (from $149)
9. Savannah, Georgia
You might not immediately think of the South for a fall getaway, and in Savannah, you certainly won’t need to bundle up like a character in a Nora Ephron movie. However, this enchanting city perfectly embodies the romantic atmosphere and coziness we cherish in her films. Put on your walking shoes and start your day at City Market, a vibrant central hub filled with shops and restaurants, which is a great launching point for your adventures. Nearby, River Street and Broughton Street offer excellent opportunities for shopping and discovering Savannah’s culinary delights. Don’t miss Forsyth Park, where you can admire the golden leaves while enjoying a stunning backdrop for your stroll. Savannah also boasts a wealth of historic homes to tour, such as the Davenport House Museum and the Green-Meldrim House.
Where to stay: River Street Inn (from $107 a night), Perry Lane Hotel ( from $246)
10. Washington, D.C.
With its historic architecture and vibrant fall foliage, D.C. is definitely worthy of Nora Ephron’s feature film treatment. Of course, the city has no shortage of museums to visit, as well as landmarks like the Washington Monument, the National Mall (a great place for views of the leaves), the Capitol building, and The White House. You also can’t miss exploring the idyllic Georgetown neighborhood. Here, you can wander down picturesque European-style streets, pop into a mix of local boutiques and well-known stores, and enjoy a variety of dining options. I can easily envision a Nora Ephron lead living in this delightful area. While in Georgetown, be sure to explore the stunning Georgetown University campus. Just outside of D.C., Old Town Alexandria offers even more fall energy. A quick train ride will take you to this quaint town, where you can soak up the small-town charm and centuries-old architecture.
Where to stay: The Tabard Inn (from $152 a night), The Poppy Georgetown (from $164)
ABOUT THE AUTHOR
Lauren Blue, Lifestyle Staff Writer
As a Lifestyle Staff Writer for The Everygirl, Lauren ideates and writes content for every facet of our readers’ lives. Her articles span the topics of home decor, delicious recipes, hobbies, travel itineraries—and everything in between. When she isn’t testing the latest TikTok trend, she can be found scouring Instagram for beautiful homes to feature on the site.
