Start Labor Day Weekend off right with river views, southern soul, and rooftop vibes. Labor Day Weekend in Montgomery, Alabama, shouldn’t start on Saturday, which is why we are offering you some evening and late-night options to unwind and enjoy Friday. We packed the day with unforgettable experiences that blend riverfront fun, happy hour flavors, minor league baseball, and R&B beats.

Afternoon: Rooftop Views & Local Pours

Before the night comes alive, let the stress of the week melt away as you ease into the weekend at one of Montgomery’s golden-hour hotspots.

Golden Happy Hour at Bar Attico
Rooftop of Ravello | 4:30 PM – 6:30 PM
Unwind above the city with sunset views and rooftop sips during Bar Attico’s “Golden Happy Hour.” Enjoy cocktail specials, breezy vibes, and a laid-back atmosphere as the sky lights up in shades of gold and orange. It's the perfect pre-dinner scene for friends or couples looking to toast to the weekend.

Hilltop Public House
3 North Goldthwaite Street | 3–6 PM
Nestled in historic Cottage Hill, Hilltop Public House tempts with house-made bagels, artisan coffee, craft cocktails, and handpicked wines. Their happy hour is lively and has gained local-favorite status, offering drink specials and karaoke (starting at 7 pm) that set the perfect tone for a carefree weekend.  Soak up the good vibes and mingle with fellow revelers before the night unfolds.

Early Evening: Baseball & Giveaways or Cruise into the Night

Want to skip baseball? Scroll down for river cruise options starting around the same time!

Montgomery Biscuits vs. Biloxi Shuckers
Riverwalk Stadium | First pitch at 6:30 PM
For a family-friendly way to start the weekend, catch the hometown Biscuits as they take on the Biloxi Shuckers in one of their final home games of the season. The first 1,000 fans of all ages will score a limited-edition Patch Hat, so get there early! Experience all the minor league charm at the Riverwalk Stadium, named Newsweek’s Best Double-A Ballparks of 2025, so enjoy the game, food, and yes, flying biscuits. If you don't catch them Friday night, they play at home in Montgomery all weekend!

River Adventures for Every Vibe

If you and your crew prefer drifting on the water to cheering from the stands, Montgomery offers two river cruises to match your mood:

Sip-n-Cycle Football Party Cruise
Departures from 11:00 AM to 8:45 PM from Riverfront Park
Start your long weekend with a 90-minute pedal-powered river cruise designed for football fanatics and party enthusiasts. Sport your team colors, bring your favorite snacks and drinks, and gear up for a floating game-day celebration. This is tailgating reimagined, set on the Alabama River and pulsing with team pride.

Harriott II Friday Night Dinner Cruise
7:00 PM – 9:00 PM | Boarding at 6:15 PM
This Friday Night Dinner Cruise on the Harriott II Riverboat is your ticket to a double delight: a delicious Southern buffet and live entertainment, all while gliding past sweeping river views. It’s a classic Montgomery experience, perfect for couples or families ready to relax and soak up every moment.

Nightlife Entertainment with Southern Soul

R&B and Southern Soul Music Fest
Montgomery Performing Arts Centre | 8:00 PM
Take your Friday from happy hour to high-energy as you cap off the night with a powerhouse concert featuring Calvin Richardson, Q Parker, Cupid, 69 Boyz, Mike Clark Jr., Toy Toy, and the electrifying MC Lightfoot. Enjoy smooth vocals, irresistible rhythms, and a crowd that just can’t stop moving. If you’re still riding the excitement from earlier, this is where you’ll want to let loose.

Dinner Options to Wrap the Day

When hunger strikes, Montgomery’s dining scene rises to the occasion with bold flavors and vibrant settings that keep your night’s adventures going:

Ravello Ristorante
Located in a beautifully restored historic downtown building, Ravello specializes in coastal Italian cuisine, featuring fresh seafood, house-made mozzarella and burrata, and bright flavors like lemon and citrus. Dishes like scialatielli di mare (shrimp, clams, mussels with fresh noodles) and daily‑made pasta shine. It’s elegant yet approachable, perfect for a refined dinner before a cruise or show.

Central
A gem in Montgomery’s downtown entertainment district, Central offers a creative take on Southern‑inspired American fare. Think Gulf seafood, local meats, and seasonal greens served in a dramatic brick‑walled space with open wood‑fire cooking. Star dishes include pork tenderloin, ribeyes, boudin croquettes, and fried green tomato starters.

The House Restaurant at the Renaissance
Located in the Renaissance Hotel in downtown Montgomery, The House blends contemporary Southern cuisine with Cajun and Creole influences. Favorites include crisp salads, prime steaks, and creative entrée options in a polished, hotel‑member ambiance. Casual Southern hospitality meets refined menu execution here.

Saturday is your day to do something new or revisit a place in Montgomery you haven't been to in a while; it is a perfect blend of community, culture, and celebration. Saturday is your chance to experience Montgomery’s soul from sunrise to moonlight.

Morning: Markets & Local Flavor

EastChase Farmers Market
7:00 AM – 12:00 PM | Near Sephora & H&M at The Shoppes at EastChase
Start your Saturday with fresh air and fresher finds at the EastChase Farmers Market, one of Montgomery’s most popular weekly events. With over 20 certified local vendors, this market is stocked with everything from vine-ripened produce and homemade jams to locally harvested honey and some of the best boiled peanuts in the South. Grab a coffee, bring a tote, and enjoy the neighborly charm of this rain-or-shine market that’s as much about connection as it is about food. Pro tip: Arrive early for the best selection!

Afternoon: A Powerful Screening Tribute 

Black Angels Over Tuskegee
Troy University Davis Theatre | Showtimes at 3:00 PM & 7:00 PM
Take a meaningful break from the weekend's buzz with a screening of the true story of the Tuskegee Airmen, the first African American fighter pilots in U.S. history. Black Angels Over Tuskegee brings their legacy to life with passion and purpose, making it the perfect cultural experience for families, history buffs, and anyone looking to reflect and honor.
Choose the 3 PM matinee for a slower-paced day or the 7 PM performance after the pep rally to wind down the evening.

Evening: Red Tails Classic Pep Rally

Red Tails Classic Pep Rally
Riverfront Park | 6:00 PM – 10:00 PM
There’s no better way to wrap up your Saturday than with a citywide celebration of HBCU pride and military heritage. Kick off the evening with a Salute to the Tuskegee Airmen and the 187th Fighter Wing, followed by a full-on pep rally for Tuskegee University and Winston-Salem State University. Expect live music, food trucks, marching bands, and an electric crowd decked out in team colors. It’s family-friendly, full of community spirit, and the ultimate warm-up for Sunday’s big game.

Dinner Recommendations Before or After the Pep Rally

Taste at Hampstead Happy Hour
Taste Hampstead | 3:00 PM – 6:00 PM
If you’re on the east side, swing by Taste in Hampstead for a curated happy hour experience. With select wine and beer specials and a relaxing patio, it's the perfect place to sip, savor, and socialize before heading out for evening activities.

D'Road Cafe
This cozy downtown café offers a taste of authentic Venezuelan and Latin home cooking, served in a space that feels like a friend’s kitchen. Savor pabellón criollo with tender brisket, fluffy arepas, and sweet tea. Every bite is a celebration of warmth, heart, and vibrant flavor.

Vintage Year
Located in the Old Cloverdale district, this local favorite began as the city's only specialty wine shop and has since evolved into an upscale dining destination. The menu features seasonal fresh‑catch seafood, hand‑cut butcher’s meats, and innovative entrees; all served with attentive service and curated wines and spirits. Celebrated by outlets like USA Today, Garden & Gun, and the James Beard Foundation, it's the perfect elegant choice for a memorable dining experience.

Double Down Bistro
If you’re craving a late dinner after the pep rally, Double Down Bistro is the spot to end your night on a high note. This local favorite is known for its lively energy, mouthwatering Southern comfort food, and standouts like their fried chicken and fried green tomatoes. The inviting, upbeat atmosphere makes it the perfect place to relax, recharge, and enjoy the final moments of your evening.

Labor Day Sunday in Montgomery is a day made for ending summer on a high note.

Morning: Brunch & Music by the Rapids

Montgomery Whitewater Brunch + Patio Music
Montgomery Whitewater | 11:00 AM – 2:00 PM
Kick off your Sunday with a fresh brunch at Eddy’s Restaurant & Bar, located right at Montgomery Whitewater. Enjoy delicious brunch classics served all day, accompanied by live patio music for the perfect laid‑back soundtrack. Whether you sit inside or on the scenic patio overlooking the rapids, it's a winning combo of good food and great views.

Afternoon Feature: Football Meets Legacy

Red Tails Classic
Cramton Bowl | 6:00 PM
Head to the iconic Cramton Bowl for the Red Tails Classic, where Tuskegee squares off against Winston‑Salem State this year. This isn’t just football—it’s a tribute to the legacy of the Tuskegee Airmen, filled with marching bands, spirited fans, and compelling halftime moments. Get ready for an evening of high energy, big pride, and celebration. 

Night Lights: Country, Soul & R&B Under the Roof

Labor Day Live! w/ Kirk Jay
BB King’s Blues Club | 8:00 PM
Spend your night with good food and even better music. Kirk Jay is back on the Montgomery stage, delivering powerhouse vocals fresh from NBC’s The Voice. He’ll be joined by Lady K, Alabama’s own soul queen, and the event is hosted by the hyped DJ Freaknazty. Expect a tight blend of country, soul, and R&B. This is how you close out a long weekend with a celebration. 

Sunday Evening Dinner Recommendations

Firebirds Wood Fired Grill
Located at the Shoppes at EastChase, Firebirds serves bold, American steakhouse flavors in a stylish yet welcoming atmosphere. Known for its hand-cut aged steaks, fresh seafood, scratch-made cuisine, and signature cocktails, it's a go-to for locals and visitors alike. Open until 10 PM on Sundays, it’s a perfect stop whether you're catching dinner before a show or leisurely closing out the evening.

End your three-day weekend with a day full of action and live music—all wrapped up with fun at a local favorite spot.

Morning & Afternoon: Golden Hour Festival at Montgomery Whitewater

Golden Hour Labor Day Festival
Monday, Sept 1 | 7:00 AM – 8:00 PM
Montgomery Whitewater continues the festive vibes with the Golden Hour Labor Day Festival. This is a two-day festival that begins on Sunday. With plenty of festivities to cap off the weekend with whitewater thrills, live music, races for every age, and plenty of food and family fun. The Golden Hour Festival is Montgomery Whitewater's signature way to say goodbye to summer, and it is a day full of adrenaline and community spirit as they host three crowd favorites:

• Golden Hour 5K (7:00 AM): A professionally timed run that’s open to all ages and paces and features awards across 5-year age groups, finishing with a beverage and race T-shirt.
• River & Trail Triathlon (8:00 AM): A multi-sport challenge for ages 12–17, with a run, bike ride, and paddle through the wooded course—gear included for the paddle portion.
• Lil’ Triathlon (9:00 AM): Designed for kids ages 6–11, this fun-length tri adds a paddle, bike, and run—parents join the littlest paddlers if needed.

Stick around or just show up for the Breakfast of Champions buffet at Eddy’s (8:00–11:00 AM) and stay to enjoy live music, food, and post-race celebrations all day long. Plus, activity passes are discounted, and admission is free.

Sunday, Aug 31 | Sunday: 10 AM–8 PM
Sunday features discounted activities, an outfitter sale, brunch and buffet at Eddy’s, live music, a Kids’ Lot, and sunset tubing, rafting, and ropes courses.

Evening: Kick Back and Relax at Industry Night at Red Bluff Bar

Industry Night at Red Bluff Bar at the Silos
4:00 PM – 10:00 PM (Karaoke 6:30 PM – 9:00 PM)
End your day with laid-back fun at Red Bluff Bar, overlooking the Riverfront. If you're in the hospitality or food-service industry, enjoy 20% off drinks all evening. Warm up your vocals for karaoke powered by JayDubzComedy from 6:30–9:00 PM. It’s the perfect way to toast a weekend well spent in style.