Experience · Sanford

Sanford Theater & Southern Fare Date Night

Spend a delightful evening soaking in local culture with a show at The Ritz Theater, a beautifully restored historic venue. Afterwards, enjoy an inventive, farm-to-table Southern dinner at The Tennessee Truffle, known for its charming interior and unique dishes. Cap off the night with a relaxed drink at The Sullivan Public House.

A 4.5-hour Sanford evening plan for couples — The Ritz Theater/Wayne Densch Performing Arts Center, The Tennessee Truffle, The Sullivan Public House.

Duration: 4h 30m
Cost: $75–$150
Stops: 3 stops
Walking: Light walking · Total 0.2-mile driving route
Best time: 5:00 – 10:00 PM
Ideal for: Couples · Friends · Solo

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The plan

1The Ritz Theater/Wayne Densch Performing Arts Center(2 hrs)→
2The Tennessee Truffle(1 hr 30 min)→
3The Sullivan Public House(1 hr)

Why this plan works

The 3 stops cover about 0.2 miles total, which keeps you in one pocket of Sanford instead of crossing town between them. The Ritz Theater/Wayne Densch Performing Arts Center is the main event and takes the biggest block of time; the other stops are built around it. It finishes at The Sullivan Public House — a short, low-effort stop you can skip if you're ready to call it. Best suited to couples, friends, and solo who want a planned Sanford outing without improvising between stops.

The story

The itinerary

3 stops, one great day

1
2 hrs
The Ritz Theater/Wayne Densch Performing Arts Center
Arts & Culture
Latest incarnation of a historic, intimate 1923 theater now hosting plays, concerts, dance & events.
What to do — Catch a captivating play, concert, or dance performance in the intimate setting of this historic 1923 theater.
Scout Side Quest
Look around the historic theater and pick your favorite vintage detail before finding your seats.
0.1 mi · 3 min walk or 3 min drive
Then Take a short walk around the corner to your dinner reservation.
2
1h 30m
The Tennessee Truffle
Food & Drink
Relaxed eatery with a charming interior specializing in inventive, farm-to-table Southern fare.
What to do — Savor inventive farm-to-table Southern fare and experience exceptional dining in a relaxed, charming interior.
Scout Side Quest
Scan the menu and secretly pick the dish you think your date would love most. Reveal your guesses together.
0.1 mi · 3 min walk or 3 min drive
Then Walk a block to grab a nightcap nearby.
3
Optional 1 hr
The Sullivan Public House
Nightlife
What to do — Optional nightcap for those who drink — skip it and the plan still works. Find a cozy spot for a post-dinner drink to discuss the show.

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The route

On the map

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Common questions

Planning this outing

Is this a good Sanford itinerary for couples?: Yes. It's built for couples, friends, and solo and runs about 4 hr 30 min across 3 stops, starting at The Ritz Theater/Wayne Densch Performing Arts Center.
How long does this outing take?: Plan on 4 hr 30 min door to door, including time between stops.
How much does this Sanford itinerary cost?: Roughly $75–$150 per person, before parking and tips. Free and low-cost stops are marked on each card.
Is this itinerary walkable?: Yes — every hop is under a mile, about 0.2 miles of walking in total.
Do I need reservations?: No. Every stop on this plan takes walk-ins, though weekends move faster if you arrive early.

Keep exploring

Different moods, same city.

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Arts & Culture
Sanford
Sanford Historic Stroll & Casual Dinner
Enjoy a free and captivating evening stroll through Historic Downtown Sanford, taking in the unique architecture and local atmosphere. Afterwards, head to Henry's Depot for an affordable and diverse dinner, followed by a leisurely browse through Maya Books & Music.
Duration
3h 30m
Cost
$20–$50
Ideal for
Friends · Solo
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