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Virginia Day Trips and Chesterfield Base: Dog-Friendly Adventure with Free Breakfast (July 28 - August 2, 2025)

Viewed by 79 travelers

Day 1: Richmond Exploration

Richmond, VA on July 28, 2025

8:00am

Hotel Breakfast

Enjoy a complimentary dog-friendly breakfast at your hotel in Chesterfield, providing energy for a day exploring Richmond.
Included, 1h0m

9:30am

Virginia State Capitol

Tour the historic Virginia State Capitol building designed by Thomas Jefferson. Open 9am-5pm. Dogs are welcome on outdoor grounds but not inside.
Free, 1h30m

11:30am

Walk the Canal Walk

Stroll along the scenic James River Canal Walk with your dog. It’s a peaceful urban trail offering views of city and river life.
Free, 1h0m

1:00pm

Lunch at Bottoms Up Pizza

Dine outdoors with your dog at Bottoms Up Pizza, known for fresh toppings and casual atmosphere in Richmond’s fan district. Open 11am-10pm.
USD15-25, 1h0m

3:00pm

Maymont Estate and Gardens

Explore the beautiful dog-friendly gardens of Maymont, though dogs are not allowed in the mansion. Opens 10am-5pm daily.
Free, 2h0m

6:00pm

Dinner at The Daily Kitchen & Bar

Casual dinner with dog-friendly patio seating offering fresh, locally sourced American dishes. Open until 9pm.
USD20-35, 1h30m
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Day 2: Williamsburg History

Williamsburg, VA on July 29, 2025

7:30am

Hotel Breakfast

Start with free hotel breakfast before heading east to Williamsburg, about 1-hour drive from Chesterfield.
Included, 1h0m

9:30am

Colonial Williamsburg Historic Area

Visit the historic Colonial Williamsburg district. Dogs are allowed on the walking paths but not inside buildings.
Free to walk; admission varies for attractions, 3h0m

12:30pm

Lunch at King’s Arms Tavern

Enjoy lunch at King’s Arms Tavern with outdoor seating; famed for colonial-inspired menus and pet-friendly patio. Open 11am-3pm.
USD20-30, 1h0m

2:00pm

Williamsburg Winery Visit

Tour the Williamsburg Winery grounds with your dog on leash; sample wine and enjoy gardens. Open 11am-6pm.
Free tours with purchase options, 2h0m

5:00pm

Return to Chesterfield & Dinner at Dog-Friendly Local Spot

Dine at Stono, known for dog-friendly outdoor dining and fresh American fare, back near your hotel. Open until 9pm.
USD25-40, 1h30m
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Day 3: Charlottesville & Monticello

Charlottesville, VA on July 30, 2025

7:00am

Hotel Breakfast

Have breakfast early at the hotel to prepare for the western 1.5-hour drive to Charlottesville.
Included, 1h0m

9:00am

Monticello Grounds & Visitor Center

While dogs are not allowed inside Monticello House, they are welcome on grounds and hiking trails. Explore the beautiful estate setting.
USD29 Adult; Grounds free for dogs, 2h30m

12:00pm

Lunch at The Whisky Jar

Enjoy Southern comfort food at this dog-friendly outdoor patio restaurant in Charlottesville’s historic downtown. Open 11am-9pm.
USD15-25, 1h0m

2:00pm

Rivanna Trail Walk

Take a relaxing walk on one of Charlottesville’s dog-friendly Rivanna Trail segments along the river and forest paths.
Free, 2h0m

5:00pm

Return to Chesterfield & Dinner at Local Eatery

Dine at Baby Bistro in Chesterfield with dog-friendly outdoor seating, offering French-inspired American cuisine. Open until 8pm.
USD30-45, 1h30m
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Day 4: Great Falls Park

Great Falls, VA on July 31, 2025

7:30am

Hotel Breakfast

Enjoy your hotel’s free breakfast to energize for a nature-focused trip to Great Falls Park near DC, about 1.5-hour north drive.
Included, 1h0m

9:30am

Great Falls Park Hiking

Explore dog-friendly trails showcasing spectacular falls and river views. Pets must be leashed. Park open 7am-sunset.
USD20 Vehicle Entry Fee, 3h0m

12:30pm

Lunch Picnic at the Park

Bring your own dog-friendly packed lunch or grab to-go from local deli in nearby McLean for a picnic amid nature.
Varies, 1h0m

2:00pm

Meadowlark Botanical Gardens

Visit this nearby gardens area where dogs on leash are welcome in outdoor areas. Open 10am-6pm.
USD10 Adult, 2h0m

5:00pm

Return & Dinner at Dogwood Dell

Relax with a dog-friendly dinner at Dogwood Dell in Chesterfield offering Southern comfort dining with pet-friendly patio. Open until 9pm.
USD25-40, 1h30m
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Day 5: Chesterfield Local

Chesterfield, VA on August 1, 2025

8:00am

Hotel Breakfast

Enjoy a leisurely complimentary breakfast at your Chesterfield hotel before a relaxed local day.
Included, 1h0m

9:30am

Pocahontas State Park

Spend the morning exploring Chesterfield’s vast dog-friendly Pocahontas State Park with hiking, lake views, and shaded trails. Open 7am-9pm.
USD7 Vehicle Entry, 3h0m

1:00pm

Lunch at Nikki’s Old Virginia Smokehouse

Enjoy authentic Virginia BBQ and outdoor seating at dog-friendly Nikki’s Old Virginia Smokehouse in Chesterfield. Open 11am-8pm.
USD15-25, 1h0m

3:00pm

Historic Chesterfield Courthouse

Visit the historic Chesterfield Courthouse grounds with your dog, a quiet place to soak up local history. Open daylight hours.
Free, 1h0m

5:30pm

Dinner at Crimson Tate

Dine with your dog on the patio at Crimson Tate, featuring contemporary American with Southern influences. Open until 9pm.
USD30-45, 1h30m
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Day 6: Virginia Beach Visit

Virginia Beach, VA on August 2, 2025

6:30am

Hotel Breakfast

Start very early with hotel breakfast and prepare for the southeast 2.5-hour drive to Virginia Beach.
Included, 1h0m

9:30am

Virginia Beach Oceanfront and Dog Park

Enjoy the dog-friendly beach areas and off-leash dog park at Virginia Beach Oceanfront. Early morning is best to avoid crowds.
Free, 3h0m

1:00pm

Lunch at Waterman’s Surfside Grille

Dine oceanside with your dog on the patio at Waterman’s, known for fresh seafood and casual vibe. Open 11am-9pm.
USD20-35, 1h0m

2:30pm

Back Bay National Wildlife Refuge

Quiet wildlife refuge near Virginia Beach that welcomes dogs on leash; enjoy peaceful trails and natural scenery.
Free, 2h0m

5:00pm

Return to Chesterfield & Casual Dinner

Return to Chesterfield and enjoy a casual dinner at Moe’s Southwest Grill offering dog-friendly outdoor seating available. Open until 9pm.
USD15-25, 1h0m
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