CHICAGO
Sat. April 4- Sun. April 5 | 2026
The Looseleaf Weekend
It’s tea time in Chicago.
This weekend in Chicago:
Tea for two: a pair of VIP tickets to Chicago Tea Week, an intimate extravaganza of slow-sipped tastings and wellness events.
Stay in one of America’s great Main Street hotels, red-bricked and grand.
A pair of pies from one of the best spots in Texas. Have your pick from their very long list of pie possibilities.
As always, your stay, meal and local experience are all bookable in one click.
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Why here?
“Imagine debarking from a long train ride to walk into the Redlands Hotel’s dining room and an elegant dinner,” writes the hotel about its own rail-rich 19th century history.
And that’s pretty much our exact notion for this weekend: a train ride into the freshly-blossomed Piney Woods, a good springy meal, and a late-afternoon return to the elegance of the Redlands Hotel in the heart of town.
Because Palestine, Texas, is essentially perfect overnight material. We don’t really have strict parameters for what that is, but the closest definition is that a short escape should have a certain bubble-feeling to it. It should be a place with a quality that exists only right there, in those few square miles, and exactly nowhere else.
Read on or
Image via The Redlands Hotel
Palestine sits somewhere in a nether-municipal category between town and city. It’s compact, it’s walkable, it has a kind of precise local color and depth of personality. And best of all is that this place has a thing.
This is a railroad town. Palestine’s rapid growth through the mid-1800s was a product of the ever-elongating Texas rail lines, built spike by spike, across the hilly eastern quarter of the state.
In the 1870s, the International and Great Northern Railroad built a major hub here, and some considerable wealth rolled in.
Brass from the railroad companies built a row of many-eaved mansions along Sycamore Street (still there and beautiful today), and an infusion of culture took up residence too.
So Palestine has history for sure — and 1,800 registered historic sites — but more than that, there’s character.
There’s the Main Street and Old Town, and the Texas Theatre’s vintage-red marquee, and the Anderson County Courthouse columns. There are the dogwood trails and the Curious Museum, and a pepper festival every fall.
But set into the soul of here is the railway.
“Once again,” writes the hotel of its smartly renovated building, “a visitor can walk into the Redlands dining room for a fine meal, historical surrounding and perhaps learn a new story about this town.”
This weekend in Palestine, TX, discover…
The stay.
Photo via The Redlands Hotel
The Redlands Hotel
Opened in 1915, the Redlands is a five-story Renaissance Revival brick building that was built as a confidently cosmopolitan hotel in a town that knew it would need one.
In addition to its hospitality duties, the railroad ran their operations from these hallways all the way through the 1950s. Today, there are 20 suites and a wealth of railroad photographs and memorabilia.
The speaker at the 1915 grand opening predicted the hotel would "stand a century hence as a work of art." Here we are.
Suite pre-paid for Saturday night. Sleeps two.
The day.
Photo: "Rusk Depot Platform" by Larry D. Moore
Easter Lunch in the Piney Woods (by Rail)
Whistle off on a four-hour round trip excursion — aboard vintage cars — through 25 miles of East Texas’s Piney Woods. The train is virtually sold out, but you’ve got First Class seats for two.
There’s champagne at departure and a catered Easter meal at the Rusk depot by the lake. The dogwoods peak in March along these tracks; full disclosure, they may be giving way to green by now, but the woods are still something.
On the menu: smothered chicken and baked ham. Dessert is banana pudding.
Lunch for two, served mid-way through your route. Includes a champagne toast and appetizer at departure. Pre-paid for Saturday morning at 11am
The find.
Image via Duncan Depot/Instagram
Duncan Depot
10,000 square feet of antiques is what it is. There’s everything from primitive to mid-century wares, all housed in a just-right-looking building on West Main that has been a commercial anchor since 1885.
It’s consistently voted Palestine's best antique shop, which tells you something, because this town has an antique shop or two.
Duncan is closed on Sunday, so the time to sneak it in may be right after your train returns to Palestine around 3pm.
The food.
Just look at the elevation of this.
Image via Oxbow Pies/Instagram
Oxbow Pies
A top pie destination in Texas, per Texas Highways Magazine; it’s a hidden gem (not our favorite description, but it’s everywhere) says Texas Monthly, and it was named as having among the best pies in the South, by no less a South authority than Southern Living.
The pie, by about a million accounts, is incredible. You have your choice of two of these much-documented pies. Like a lot of places in town, Oxbow won’t be open on Sunday, and they close before you’re back from your train-lunch. But we have a plan to get these pies to your hotel.
Your pick of whole pies, two of them, are included here. We’ll reach out to get your selections after booking.
The tucked away.
Photo via Visit Palestine
Davey Dogwood Park and the Fairy Trail
The whole thing started over coffee in 1938, when two Palestine businessmen agreed their town should have a dogwood trail.
The community found a plot of dogwoody land north of town, borrowed trucks, brought axes and hoes, and cut a proper trail through the trees.
Today there’s also a Fairy Trail flanking the dogwoods: locals build miniature worlds into tree stumps and root systems, made almost entirely from natural materials.
The evening mood.
Image via Queen St. Grill
Queen St. Grill
The hotel bar is the place on Saturday evening. Simple, short, non-overwhelming cocktail list; maybe try the Midnight Train: vanilla vodka, Kahlua, Baileys,simple syrup and cold brew.
Book it all in a click.
This Overnight includes:
Your stay at The Hotel Redlands Reserved for Saturday, April 4, 2026. Sleeps two. Already paid for, ready to check in.
Lunch mid-journey on the Texas Railroad as part of a four-hour roundtrip trek into the Piney Woods.
Two, count ‘em, two pies from Oxbow Pies. Your train schedule won’t allow you to stop in this weekend, but we’ll do everything we can to get these pies to you at your hotel.
This Overnight is no longer available. Get the next one in your inbox.
Photo credits for this story.
Images in our stories may be sourced from publicly available materials, and are used to represent places as they exist. All rights remain with their respective owners.