Filtered to Washington, DC. Switch origins below. Showing train and drive trips only.
19 picks across the catalog.
The handful we keep coming back to.
Old streets, new restaurants, the kind of walking that earns dinner.
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Three hours south, a city that still has bookstores with chairs and restaurants that don't take reservations. Powell's until your feet hurt, natural wine in a former garage, a hotel that remembers when Portland was weird before it was a brand.
Three hours north on the Cascades, you step off into a city where the mountains meet the water and nobody's pretending it's casual. Granville Island for lunch, Stanley Park when the light's right, dinner in Gastown where the servers know wine regions by soil composition.
Two hours south to a town that figured out how to be more than Monticello. The Corner for college-town energy, the Downtown Mall for dinner that matters, and enough vineyards within 20 minutes that you can pick the one where nobody's wearing a sash.
Two hours up the Hudson, you walk off the train into a town that figured itself out. Warren Street is the whole point — antiques, ceramics, a wine bar where the bartender knows what you want before you do. No car, no plan, no rush.
Sand, oysters, the kind of porch where the day just goes.
Two hours down the coast to a one-square-mile village where the sidewalks are optional and the cypress trees do more work than the marketing. Stay at La Playa Carmel — the 1904 estate where Doris Day used to live upstairs — and spend a weekend walking to everything that matters.
Three hours north on the Cascades, you step off into a city where the mountains meet the water and nobody's pretending it's casual. Granville Island for lunch, Stanley Park when the light's right, dinner in Gastown where the servers know wine regions by soil composition.
Three hours north of San Francisco, Mendocino sits on bluffs above the Pacific with no beach access and no apologies. The town is eight blocks of carpenter gothic and redwood water towers. Go in October when the fog's back and the crowds aren't.
90 minutes up the coast to a town that figured out how to be both a beach town and a wine town without losing either. Red tile roofs, white stucco, a harbor that still works. The American Riviera label is lazy — Santa Barbara is better than that.
Two hours and a ferry ride to the island that empties out after Labor Day and becomes itself again. Grey shingles, cobblestone Main Street, a harbor that still smells like a harbor. The Wauwinet is open through October and knows what it's doing.
A Mississippi River town that peaked in 1850 and knows it. Main Street still runs on brick and iron storefronts, the best hotel is an 1855 mansion on a hill, and the whole town shuts down by 9pm in a way that feels like the point. Go in October or March when the tour buses stay home.
Trees, trails, fires, fewer people. The cabin kind of weekend.
A mountain town at 4,118 feet where Atlanta people go to disappear for a weekend. Main Street antiques, waterfalls that require actual hiking boots, and the Old Edwards Inn holding down the center like it has since 1878. Go in October when the fog rolls in at 4pm and the town earns its name.
Two hours down the coast to a one-square-mile village where the sidewalks are optional and the cypress trees do more work than the marketing. Stay at La Playa Carmel — the 1904 estate where Doris Day used to live upstairs — and spend a weekend walking to everything that matters.
Three hours north on the Cascades, you step off into a city where the mountains meet the water and nobody's pretending it's casual. Granville Island for lunch, Stanley Park when the light's right, dinner in Gastown where the servers know wine regions by soil composition.
Three hours north of San Francisco, Mendocino sits on bluffs above the Pacific with no beach access and no apologies. The town is eight blocks of carpenter gothic and redwood water towers. Go in October when the fog's back and the crowds aren't.
A Mississippi River town that peaked in 1850 and knows it. Main Street still runs on brick and iron storefronts, the best hotel is an 1855 mansion on a hill, and the whole town shuts down by 9pm in a way that feels like the point. Go in October or March when the tour buses stay home.
Out and back. The whole point is leaving.
Drafted by our agent, kept on the list when they hold up. Labeled honestly.
Thirty miles up the Hudson, a working farm with a restaurant that redefined American cooking and a lodge you didn't know you could stay at. One night gets you the farm-to-table tasting menu that earned the hype, the sunrise walk through the greenhouses, and the kind of meal-driven reset that costs half what it would in the city.
An hour south of Portland, the valley that makes the Pinot Noir Oregon is known for. Small-production wineries you visit by appointment, a farm-to-table dinner scene that predates the term, and a restored farmhouse hotel where the breakfast eggs come from the property. Two nights gets you four wineries, one long lunch, and the version of wine country that hasn't been Napa'd yet.
An hour east of Portland on I-84, where the Columbia Gorge turns into a wind tunnel and the town that grew up around it knows exactly what it is. Kiteboarding if you're into it, wine tasting if you're not, a hotel with a rooftop bar where you watch both happen at once.
Texas Hill Country wine town an hour west of Austin. German bakeries at 7am, limestone tasting rooms that close at 5pm, a Sunday drive home through wildflowers if you time it right. Two nights gets you past the Main Street tourists and into the vineyards that don't advertise.
A college town that grew up without losing the farmer's market. Two and a half hours from Chicago gets you Saturday morning on the Capitol Square with cheese curds that cost $4 and taste like the reason Wisconsin matters. Stay on the isthmus, walk the lakes, eat dinner at a restaurant that would work in any city but costs what it should here.
Pennsylvania wine country an hour west of Philly. Chaddsford and Galer Estate make wines that don't apologize for not being Napa. Sleep at an 18th-century inn with a Michelin-starred restaurant, walk the Wyeth museum grounds, eat lunch at a farm stand that becomes dinner conversation.
Pennsylvania wine country nobody talks about yet, with a main street of antiques dealers who actually know what they're selling. Two hours from Newark gets you a weekend of Chambourcin that costs what it should, mid-century chairs you can still afford, and a dinner at a farm restaurant that would have a Michelin star if it were 90 miles closer to the city.
Two nights in Rhinebeck — a town that runs on Main Street bookstores and farm-to-table restaurants that don't feel like a trend anymore. Sleep at a converted 1766 inn, eat dinner at a place that sources from three farms within ten miles, drive home Sunday with a trunk full of apples you picked yourself.
A mountain town at 4,118 feet where Atlanta people go to disappear for a weekend. Main Street antiques, waterfalls that require actual hiking boots, and the Old Edwards Inn holding down the center like it has since 1878. Go in October when the fog rolls in at 4pm and the town earns its name.
Three hours south, a city that still has bookstores with chairs and restaurants that don't take reservations. Powell's until your feet hurt, natural wine in a former garage, a hotel that remembers when Portland was weird before it was a brand.
Two hours down the coast to a one-square-mile village where the sidewalks are optional and the cypress trees do more work than the marketing. Stay at La Playa Carmel — the 1904 estate where Doris Day used to live upstairs — and spend a weekend walking to everything that matters.
Two nights in Yountville — the town that built itself around The French Laundry and kept going. Walk to dinner at three restaurants that take reservations, bike through vineyards that don't charge tasting fees, sleep at a hotel that understands you're not here for a bachelorette party.
Three hours north on the Cascades, you step off into a city where the mountains meet the water and nobody's pretending it's casual. Granville Island for lunch, Stanley Park when the light's right, dinner in Gastown where the servers know wine regions by soil composition.
Three hours north of San Francisco, Mendocino sits on bluffs above the Pacific with no beach access and no apologies. The town is eight blocks of carpenter gothic and redwood water towers. Go in October when the fog's back and the crowds aren't.
90 minutes up the coast to a town that figured out how to be both a beach town and a wine town without losing either. Red tile roofs, white stucco, a harbor that still works. The American Riviera label is lazy — Santa Barbara is better than that.
Two hours and a ferry ride to the island that empties out after Labor Day and becomes itself again. Grey shingles, cobblestone Main Street, a harbor that still smells like a harbor. The Wauwinet is open through October and knows what it's doing.
A Mississippi River town that peaked in 1850 and knows it. Main Street still runs on brick and iron storefronts, the best hotel is an 1855 mansion on a hill, and the whole town shuts down by 9pm in a way that feels like the point. Go in October or March when the tour buses stay home.
Two hours south to a town that figured out how to be more than Monticello. The Corner for college-town energy, the Downtown Mall for dinner that matters, and enough vineyards within 20 minutes that you can pick the one where nobody's wearing a sash.
