People on porch at Carter Mountain

Charlottesville Date Ideas for Every Day of the Week

May 31, 2022  |  Carter Mountain Orchard

Category: Local Guides

Charlottesville is known for many things: its stunning setting in the Blue Ridge Mountains, a restaurant scene that makes every foodie’s mouth water, and a bustling calendar of activities each week. Among these events are dozens of opportunities for local date nights.

If you’re hoping to do something memorable for your next date night this summer, look no further! Here are a few fun ideas for you and your special someone, right here in Charlottesville.

Monday Walks Along the Rivanna River

Riverview Park | Year ‘Round | 6 AM–9 PM

The Rivanna Trail is a paved pathway starting at Riverview Park and stretching 20 miles around the City of Charlottesville. Everything about this nature trail makes it ideal for a peaceful date night: the trickling sounds of the river, the birds happily chirping above, and especially the way the sun peeks through the trees at sunset.

At Riverview Park and the surrounding trail, visitors are invited to walk, run, bike, fish, or bird watch. No reservations or tickets are required to visit. Plus, The Wool Factory is just around the corner for a post-walk coffee!

Rivanna River walk from Riverview Park

Tuesday Night Trivia

Firefly Restaurant & Game Room | Year ‘Round | 8–10 PM

Think you’re clever? Test your knowledge at Firefly’s trivia night every Tuesday from 8-10 PM! Each week, trivia enthusiasts compete to correctly answer nearly 70 tricky questions for the chance to win a prize. Themes rotate weekly so that brainiacs of all interests have something to contribute. Yes, that means both history buffs and musical geniuses have the chance to succeed!

Trivia is free, although participants are encouraged to make a dinner reservation to guarantee their spot. It’s all fun and games until you plan to join and can’t find a seat for you and your date!

Firefly restaurant trivia sign

Wind Down Wednesdays

Carter Mountain Orchard | June 1–August 31, 2022 | 6–9 PM

As Charlottesville natives, we’re no strangers to the area’s jaw-dropping scenery. In fact, every Wednesday during the summer, we invite visitors up the mountain to unwind with acoustic music and a calming midweek sunset. It’s the perfect way to spend the evening!

Visitors will often enjoy sweet snacks from the Apple Barn (ahem, apple cider donuts), dinner from a local food truck, plus refreshing beverages from the Carter Mountain Wine Shop and Bold Rock Tap Room.

Wind Down Wednesday at Carter Mountain

Tickets are $5 and should be reserved in advance.

Thursday Evening Sunset Series

Carter Mountain Orchard | May 5–September 9, 2022 | 6–9 PM

The fun continues the following night during our Thursday Evening Sunset Series. Each week, visitors join us to dance to their favorite tunes from local performers, all while enjoying the best view of a sunset from anywhere around!

The 2022 season line-up features a rotation of local artists including Jon Spear Band, FarAway, Root Cellar Remedy, The Jackwagons, and many more. To add to the excitement, we’ll also host a rotation of local food trucks—including Vision BBQ, Sweet Jane’s Kitchen, and Good Waffles & Co.—throughout the season.

Tickets are $10 per person. Reserve them in advance because spots fill up quickly!

Thursday evening sunset series at Carter Mountain

Fridays After Five

Ting Pavilion | April 15–September 9, 2022 | 5:30–8:30 PM

If you’re looking for a C’ville tradition to share with your significant other, this is the one! As the name suggests, Fridays After Five is Charlottesville’s weekly concert series that is hosted every Friday…just after five o’clock. Social by nature, this event makes for a unique and low-pressure date night. Half the city is there, after all!

During the summer, community members meet at Ting Pavilion for live music from local performers, craft beverages, and even a few food trucks. Admission is free—just go down to the Downtown Mall to join the fun!

Aerial shot of Ting Pavilion

Looking for a laid-back Friday date? Watch the summer sun descend behind the Blue Ridge Mountains and enjoy live music at Chiswell Farm & Winery’s Summer Sundown in Greenwood!

Saturday Date Night In

Skip the hustle and bustle of downtown Saturday nights by hosting a date night at home! Weekends are the perfect opportunity to pick up a bottle of Carter Mountain Wine and cook up some local food to share in the comfort of home. Maybe even add in a movie to top it all off!

Experience the true taste of the city by picking up dinner ingredients from local vendors that morning at Charlottesville City Market. Of course, we’re there most weeks to satisfy your sweet tooth with plenty of apple cider donuts and homemade fudge for dessert.

Carter Mountain wine lineup

Sunday Salsa

IX Art Park | Year ‘Round | 7–10 PM

Want to try a new out-of-the-box activity? After kicking off in 2001, Sunday Salsa is Virginia’s longest, continually running salsa dance party! It’s a wonderful way for the community to explore dance in a fun, carefree environment.

For those with two left feet, the event starts with a dance lesson by Edwin Roa of Zabor Dance. Once everyone has the chance to get their footing, the party begins! Tickets are $8 per person ($6 for students) and can be reserved online.

Sunday Salsa at IX Art Park

There you have it: a Charlottesville date night for every night of the week! With so many unique local events, there’s always something fun to do. Plus, we’re open daily when you want to kick back and admire the best view around.