Chesapeake · Chesapeake City County, VA

Road trips from Chesapeake

Scout analyzed 59 Chesapeake places and surfaced the ones that actually fit road trips.

Places analyzed

Matches

Typical spend

$35

Typical visit

1.3 hr

Scout-verified spots

Greenbrier West

Great Bridge Lock Park

Great Bridge Lock Park is suitable for a 2-hour family outing or solo adventure, offering a playground, fishing, and scenic views, making it a free, relaxed outdoor activity. It pairs well with a picnic or a stop during a longer drive.

OutdoorsAnimalsViews

$0 typical1.5 hr visiteasy parking

Greenbrier East

Fun Forest Playground

This playground is ideal for a free family outing with young children, typically lasting 1-2 hours. It pairs well with a picnic or a walk in the surrounding city park.

OutdoorsPlayfulRelaxed

$0 typical1.5 hr visiteasy parking

Pleasant Grove West

The Bypass 168

The Bypass 168 is suitable for a casual American meal, fitting for a lunch or dinner outing with family or friends. Expect to spend $15-35 per person and stay for about an hour.

FoodCocktailsRelaxed

$15–$35 typical1.5 hr visiteasy parking

Greenbrier East

Pale Horse Coffee - Summit Pointe (Greenbrier)

This is a good spot for a quick coffee break or a quiet solo work session. Expect to spend 30-60 minutes and $5-15 per person.

FoodShoppingRelaxed

$5–$15 typical45 min visiteasy parking

Great Bridge

Pale Horse Coffee - Great Bridge

A typical visit to Pale Horse Coffee is suitable for a quick stop for a drink or light snack, lasting about 30 minutes, with an average spend of $5-15 per person. It can be paired with local errands or a brief solo break.

FoodShoppingRelaxed

$5–$15 typical45 min visiteasy parking

Indian River

Indian River Park South Side

This park is good for a free family outing or solo adventure for a couple of hours, offering hiking, biking, and a playground. It's best experienced during good weather.

OutdoorsSportsAnimals

$0 typical1.5 hr visiteasy parking

Greenbrier West

Pirate's Cove Restaurant

Pirate's Cove is a casual, family-friendly seafood spot suitable for a relaxed meal. Expect to spend 1-1.5 hours and around $15-35 per person for a typical visit.

FoodAnimalsRelaxed

$15–$35 typical1.3 hr visiteasy parking

Deep Creek South

Deep Creek Park

This park is suitable for a casual family outing or a solo walk with a dog, offering open space, a playground, and sports fields. Expect to spend 1-2 hours for free, perfect for pairing with a picnic lunch.

OutdoorsSportsAnimals

$0 typical1.5 hr visiteasy parking

Deep Creek North

Deep Creek Lock Park

This waterfront park offers a relaxed outdoor setting for families or solo visitors, good for a 1-2 hour visit with a picnic or playing at no cost. It pairs well with other outdoor activities in the Chesapeake area.

OutdoorsAnimalsViews

$0 typical1.5 hr visiteasy parking

Greenbrier West

Amber Lantern Restaurant

Amber Lantern is a waterfront dining spot best for a scenic dinner or special occasion, offering upmarket seafood and cocktails. Plan for a 1.5-2 hour visit, with typical spend between $50-$100 per person.

FoodCocktailsViews

$50–$100 typical1.3 hr visiteasy parking

Greenbrier East

Biscuit Belly - Chesapeake

Biscuit Belly is a good stop for a casual breakfast or brunch, typically taking about an hour and costing $10-25 per person. It pairs well with a morning of errands or as a relaxed start to a weekend day.

FoodRelaxedSocial

$10–$25 typical1.3 hr visiteasy parking

Greenbrier East

Black Pelican Seafood Co. Greenbrier

This is a reliable spot for a seafood dinner or lunch, costing around $30-70 per person for an hour and a half visit. It can be paired with local shopping or a movie outing.

FoodCocktailsRelaxed

$30–$70 typical1.5 hr visiteasy parking

Pleasant Grove East

Centerville Park

Centerville Park is ideal for a free family outing or solo exercise, typically lasting 1-2 hours. It's great for sports or a casual walk and pairs well with a picnic or local errands.

OutdoorsSportsRelaxed

$0 typical1.5 hr visiteasy parking

Great Bridge

Bells Mill Park

Bells Mill Park offers a 2.5-mile trail through wetlands and meadows for a 1-2 hour free outdoor excursion. It's a good spot for a walk or picnic, potentially paired with a local meal.

OutdoorsViewsRelaxed

$0 typical1.5 hr visiteasy parking

Greenbrier East

Baker's Crust Artisan Kitchen

Baker's Crust is a good spot for a relaxed meal any time of day, whether for breakfast or an casual dinner. Expect to spend $15-35 per person for a typical visit lasting about an hour.

FoodRelaxedSocial

$15–$35 typical1.3 hr visiteasy parking

Greenbrier East

Urban Hot Pot

Urban Hot Pot is good for a casual meal with friends or family, offering a interactive dining experience that can last around 1.5 hours. Expect to spend $25-45 per person, making it a good option before or after a movie or shopping.

FoodSocialPlayful

$25–$45 typical1.3 hr visiteasy parking

South Norfolk

Lakeside Park

Lakeside Park is a free outing for a relaxed hour or two, suitable for a walk, picnicking, or quiet reflection by the lake. It can pair well with a nearby meal or a longer drive for a scenic break.

OutdoorsViewsHistory

$0 typical1.5 hr visiteasy parking

Pleasant Grove West

The Barrel Room

The Barrel Room is a good stop for an evening meal or drinks, especially on weekends for live music. Expect to spend 1.5 to 2 hours and around $25-50 per person.

FoodCocktailsLive music

$25–$50 typical1.5 hr visiteasy parking

Greenbrier East

The Egg Bistro

The Egg Bistro is a reliable spot for an affordable breakfast, brunch, or casual American meal. Expect to spend about an hour here and around $10-25 per person.

FoodCocktailsRelaxed

$10–$25 typical1.5 hr visiteasy parking

Greenbrier West

Lockside Bar and Grill

Lockside Bar and Grill is a relaxed spot for American and seafood dishes, including brunch. It's suitable for a casual meal, likely pairing with a local activity, and typically costs $20-$45 per person for about 1.5 hours.

FoodCocktailsViews

$20–$45 typical1.5 hr visiteasy parking

Greenbrier East

Chesapeake City Park

Chesapeake City Park is suitable for a free outdoor family outing or solo adventure, lasting 1-2 hours. It's a good place to bring kids or dogs for some relaxed recreation.

OutdoorsAnimalsSports

$0 typical1.5 hr visiteasy parking

Victoria Boulevard Historic District

Virginia Air & Space Science Center

This science center is a good destination for a 3-hour family outing or solo visit, focusing on aerospace history and exhibits. Expect to spend around $15-25 per person, with parking likely available nearby.

ArtsHistoryViews

$15–$25 typical2 hr visiteasy parking

Fort Monroe

Firehouse Coffee 1881

Firehouse Coffee 1881 is a good stop for a casual coffee, ice cream, or pastry. Expect to spend 30-60 minutes and $5-15 per person on drinks and snacks.

FoodShoppingRelaxed

$5–$15 typical45 min visiteasy parking

Greenbrier East

Neat Bird Chicken & Whiskey

Neat Bird Chicken & Whiskey is suitable for a casual meal or drinks, offering a relaxed setting for about 1 to 1.5 hours. Expect to spend $20-$45 per person, making it a good option before or after another local activity.

FoodCocktailsRelaxed

$20–$45 typical1.3 hr visiteasy parking