Virginia boasts more than 280 wineries surrounded in plush greenery, mountain views and quaint towns. October is wine month in Virginia, there’s no better time to visit, especially with all the fun promotions and activities planned in anticipation.

Recently, we explored Middleburg, VA, it’s one of DC/VA‘s top wine destinations. Located in Loudoun County, an easy 40 minute easy drive from Dulles airport – you can rent a car or take a Uber/Lyft.

It’s the most beautiful time to explore wine country, the leaves are beginning to change and it’s very picturesque with beautiful colonial homes, antique shops and wineries. It’s also exceptionally dog friendly.

There are some really incredible properties you can’t miss, like Greenhill and Stone Tower Winery, which I could easily have spent the day at and many smaller wineries that are worth stopping by. We picked all dog-friendly wineries so we could bring Charlie, but regulations around dogs are always changing so make sure to call first and pick a beautiful day to spend outside with your pup.

How to Plan Your Trip:

There are over 50 wineries in the area, I visited 6 so there’s so much more to see and try. The Virginia Wine Board is a great resource to help plan your trip, check out their site at virginiawine.org.

Hiring a tour company is also an option, we worked with Bruce W. Schutte of Wine Pro Tours, who knows just about everything about Virginia wine, and is an exceptional resource for wineries in the area. His company picks you up from your hotel and drives you to the wineries of your choice for a very fun day of drinking without driving. Here are the wineries we visited:

Named one of the most dog-friendly cities in the US, Alexandria, VA did not disappoint. We spent the majority of the time in Old Town, a charming and walkable area filled with museums, restaurants, and great shopping. With dog bowls lining King Street, and dogs at every corner, Charlie could not have felt more at home. There’s also a free trolly that runs along King Street, which features a walkable (or trolly-able…) mile through Old Town with 200+ independently owned restaurants and boutiques.

What to do in Old Town, Alexandria, VA:

For starters, visit VisitAlexandriaVA.com or the Alexandria Visitor Center, located in the heart of Old Town at 221 King Street, they are filled with recommendations and able and willing to help you plan your perfect trip. You can also pick up a Key to the City Museum pass which is $15 ($49 value) and includes free passes to the Alexandria Black History Museum, Carlyle House Historic Park, Friendship Firehouse Museum, George Washington Masonic National Memorial Observation Deck, Lee-Fendall House Museum & Garden, Stabler-Leadbeater Apothecary Museum, Gadsby’s Tavern Museum, and The Lyceum: Alexandria’s History Museum, plus a 40% off discount coupon on the George Washinton’s Mount Vernon. Definitely call ahead to the museums for how pet-friendly they are but with Charlie in his bag, we had no problem with any of the ones listed below.

Explore the Waterfront and Founders Park

There are 18 public, off-leash dog parks in Alexandria (not including a bunch of private ones) and while I didn’t visit them all, Founders Park came highly recommended and was on the Alexandria Seaport/waterfront (which is a must visit). With riverside views of the Potomac, it’s a great place to walk the path or run around on the grass with your pup. You can book a boat ride on The Potomac Riverboat Company, which offers a variety of cruises including a 60-minute dog-friendly Canine Cruise on select days from May through September. If you’re in the mood for a picnic in the park, Society Fair and Windmill Hill Park came highly recommended. If you’re looking for a wonderful, pet-friendly seafood dining option on the water, Vola’s Dockside Grill is located in front of the Torpedo Factory Art Center on the Alexandria Seaport and is a great place to sit outside and people watch as the boats leave the marina.