Hampton Roads on the Go

2026 TWO UP WINE DOWN (A VIRGINIA WINE FESTIVAL) BUS TRIP

DEPARTURE LOCATIONS: Virginia Beach and Newport News, Virginia
DATE: November 7, 2026
COST: General Admission - $220 per person | VIP - $255 per person

Join us as we travel to the Two Up Wine Down - A Virginia Wine Festival in Charlottesville, Virginia on Saturday, November 7, 2026 for an afternoon of tastings, DJ-spun beats, and an all-star cast of curators sharing their voice and perspective through an incredible line-up of Virginia wines. The festival is all about good times, great connections, and celebrating what makes us unique. Whether you’re a wine aficionado or just down for a fun day, this is the place to be.

Prior to the Festival, we'll dine at Michie Tavern. Michie Tavern serves a daily buffet-style lunch in a rustic 18th-century-style dining room with servers in period attire. The menu features southern fried chicken, marinated baked chicken, hickory-smoked pork barbecue, stewed tomatoes, black-eyed peas, and buttermilk biscuits.

The journey itself will be a highlight, as the route through Central Virginia showcases the vibrant colors of fall—the rolling hills and mountain backdrops adorned with shades of gold, crimson, and amber. This experience allows you to relax and indulge in the festival without the concern of driving.

What: 2026 CoVa Cocktail
When: November 18, 2026 | 7-10 p.m.
Where: Rivers Casino Portsmouth Featured Spirit: Waterman Spirits

Sip and savor at CoVa Cocktail, where mixologists from local restaurants will put their best foot forward at handcrafting cocktails using products of Waterman Spirits. Guests can vote on their favorite concoction and food will be provided by Rivers Casino. Must be 21 or older to attend.

Detroit’s Greatest Musical Exports Live Onstage!

Get your seats for an evening of Motown classics as well as Christmas tunes to put you in that holiday spirit! This vibrant show features a stellar cast, backed by a top-tier band. Fans and critics love the authentic choreography, flawless vocals, and nostalgic setlist spanning fifty non-stop classics. Forever Motown provides a fun mix of classic and modern sounds that you can't help but move in your seat to!

COST: 33.05 per person (includes Ticketmaster taxes and fees).

Join us in beautiful Williamsburg, Virginia, for a festive three-day StayCation filled with holiday charm, great food, drinks, relaxation, and opportunities to connect with fellow Pack members.
We’re putting the finishing touches on our full schedule, but you can book your hotel room and reserve your spot for our exclusive Speakeasy experience now (see the separate Meetup for information on the Speakeasy experience at The Study)!

Williamsburg Lodge, Autograph Collection

Experience the charm of Williamsburg during the holiday season! The Williamsburg Lodge is beautifully decorated for the holidays, creating the perfect backdrop for a festive New Year’s getaway.

Special Pack Rate: $199 per night (excluding taxes, fees)

Rooms at this special rate are limited. We encourage you to book early rather than wait for the complete StayCation schedule to be released.]