There is a well-worn theory that a romantic Alabama weekend means sand and sugar-white beaches. A recent anniversary trip argues for the inland route: a weekend built around live theater in Montgomery, college-town history in Auburn and a garden-side brunch in Opelika — three stops that make Lee County and its neighbors one of the state’s most rewarding getaways, even for travelers who have lived on the Gulf Coast for decades.
The Play That Anchors the Trip
The reason to point the car north is the Alabama Shakespeare Festival, one of the ten largest Shakespeare festivals in the world and, since 1985, permanently housed in the Carolyn Blount Theatre in Montgomery’s Winton M. Blount Cultural Park. The theater itself is a gift story: it was built on a $21.5 million gift from Mr. and Mrs. Winton Blount, a performing-arts complex set in a 250-acre landscaped park, and it contains two stages — the 792-seat Festival Stage and the 225-seat Octagon Theatre. Staging more than 400 performances a year for audiences from more than 60 countries, ASF ranks among the largest Shakespeare festivals in the world and typically produces six to nine shows annually.
This winter the Octagon hosted “The Lehman Trilogy,” Stefano Massini’s sweeping drama adapted by Ben Power, which ran from January 29 through February 15. The production traces the Lehman brothers — Jewish immigrants from Bavaria who opened a small general store on Montgomery’s Commerce Street in the mid-1800s — from selling fabric and cotton to building the Wall Street firm that shaped, and later shook, global finance. Three actors carried the three-hour evening on the Octagon Stage, narrating the family’s story with warmth and humor and taking on the full supporting cast between them. Montgomery history is woven through the play itself: the Lehman brothers were Cotton Belt entrepreneurs whose firm helped bankroll the rise of the city before it grew into the global financial house whose 2008 collapse made the name infamous.
The production has concluded, but the lesson of the weekend holds: check ASF’s season calendar first and build the trip around a performance. The theater’s 2026-27 season was announced in May, and matinee seats in either house are comfortable ones — an easy sell for anyone, but especially for couples who want one unmissable event to organize a weekend around.
A Dormitory Turned Boutique Hotel in Auburn
From Montgomery, the drive east to Auburn takes about an hour, and the town rewards an overnight. The Collegiate Hotel, a boutique hotel steps from the Auburn University campus, occupies a former fraternity building and makes an ideal base — the staff will steer you to where the locals eat breakfast (a certain chicken-and-waffles spot just off campus fills fast on Saturdays), and, as it happens, the lobby holds a working archive: Auburn’s collegiate yearbooks, organized by date back to 1915, open to guests who ask.
That mattered on this trip. A traveler who grew up in West Virginia in the 1970s may remember a mother who drove her Ford station wagon to a family reunion in Auburn, bursting with pride to introduce her children to her first cousin — Bob Davis, then the head coach of Auburn’s basketball team. Davis led the Tigers from 1973 to 1978, five seasons that included recruiting the players who would soon take Auburn to its first NCAA tournament. Auburn’s Tiger Trail — the sidewalk memorial with bronze plaques honoring former players and coaches embedded along the town’s walkways — is the perfect place to go looking for names like that, and the hotel’s yearbooks filled in the rest. For anyone with even a thread of Auburn or Alabama history in the family, a campus weekend is a genealogy field trip waiting to happen.
Opelika’s Garden Brunch
The weekend’s other discovery is five minutes down the road in Opelika: Botanic, the lush garden-themed restaurant founded by the creator of Chicken Salad Chick. Sunday brunch here is a reservation-in-advance proposition, and the buzz is earned — a lush, plant-filled dining room, a kitchen that treats vegetables with the same ambition most kitchens reserve for steak, and prices that land below what the setting might suggest. Beyond the dining room, the property includes a Garden Shoppe and The Market, which together can eat an hour of a Sunday afternoon all on their own.
Opelika itself rewards a stroll — a revitalized historic downtown with its own restaurant row — and Auburn’s campus offers enough to fill the gaps between meals: the trees at Toomer’s Corner, the campus quads, and the Tiger Trail plaques that turn a walk downtown into a walk through a century of football and basketball history.
Why the Loop Works
The three-hour drive from Fairhope to Montgomery, and the short hop from there to Auburn, make this a genuinely doable long-weekend circuit from the coast — dinner in Auburn the first night, theater in Montgomery the next afternoon, brunch in Opelika on the way home. What makes it worth repeating is how different each stop feels from the coast: a state-class theater in a cultural park, a college town that keeps its history cast in bronze at your feet, and a restaurant that treats a Sunday like an occasion.
Anniversaries are a fine excuse. But the loop from the Bay to the Blount Cultural Park and back does not need one — it works just as well as a weekend away from the beach traffic, discovering that Alabama’s middle is full of gems of its own.