Road trip from Anchorage to Chesapeake
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Museums
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Museums
Nature & Parks
Sights & Landmarks
Nightlife
Shopping
Spas & Wellness
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Concerts & Shows
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ITINERARY
88h 19m4,461 miles31 stops
1
Fort Ward Museum & Historic Site
2
St. Paul's Episcopal Church
3
Rockwood Park
4
The Mariners' Museum and Park
Curate your Mariners’ Experience! From inspiring stories of mariners who risked it all for freedom to true tales of man conquering the wild seas, our indoor galleries will spark curiosity, wonder, and an appreciation for our shared maritime heritage. Explore over 90,000 square feet of gallery space and discover your connection to our shared maritime heritage. Admission to the Museum is only $1 per person. Add some outdoor adventure to your day in our 550-acre Park which offers visitors a quiet and serene place to walk, hike or run amongst rolling woodlands. Our Park features the award-winning five-mile Noland Trail that surrounds the 167-acre Mariners’ Lake. The Park is free and open to the public.
5
O'Connor Brewing Co.
The brewery is located at 211 W. 24th Street in the new Railroad district of Norfolk, situated next to the historic Ghent neighborshood and just a mile or two from Downtown. The Tasting Room and Production facility share a 35,000 sq. foot mid-century modern historic building. Free parking is available in their private lot or street parking is free along 24th and 23rd street. O’Connor beer drinkers come from all walks of life, but what brings them together is a love of the small, simple joys in life. The pleasure of being outdoors, relaxing on the beach with friends, having dinner with family after a day of hard work, and of course, enjoying a fresh, flavorful beer. Customers appreciate the O’Connor brand for its approachability and authenticity. They value its independent spirit, that it remains family owned and operated, and its support of the local community. And their loyalty has established it as a mainstay brand with 10 years of sustained success.
6
Girdwood Brewing Company
Enjoy local brews and epic views of the Chugach mountains at Girdwood Brewing Company. We have a beautiful timber framed taproom adorned with local art and ski relics. For those who prefer the outdoors, there’s an awesome beer garden with fire pits and plenty of seating. We offer up four core beers and a series of rotating taps. Root beer, cold brew coffee, and kombucha are available for those looking for an alcohol free beverage. Tasters and 12 ounce pours are available to drink in the taproom. If you are looking for beer to go, we fill growlers, sell 5 gallon kegs, and have 4-packs of 16 ounce cans with labels designed by Alaskan artists (for sale in the taproom only). Food trucks are on-site every day, and we have cool merchandise for you to take home. Girdwood Brewing Company is truly rooted in our community. We donate to a number of nonprofits and outdoor adventure organizations. Our brewery also provides year round employment to over a dozen locals.
7
Flattop Mountain Trail
8
Indian Valley Mine, National Historic Site
The main cabin, which contains the gift shop, and the assay building at Indian Valley Mine has some of the oldest structures built on the Turnagain Arm, and are listed as a National Historic Site. Indian Valley Mine offers visitors the opportunity to learn gold panning and browse through two historic cabins built in the early 1900's a small museum and gift shop, or simply sit back on one of our benches and take in the panoramic view of the Turnagain Arm.
9
Planet Walk
10
Four Seasons Trans Group
We provide shuttle services within Anchorage, Seward, Talkeetna, Whittier, Palmer, Wasilla, and Girdwood.
11
Acme Comedy Co.
12
Indeed Brewing Company
13
Norseman Distillery
Norseman Distillery, the first micro-distillery in Minneapolis, was founded with principles of using the very best local ingredients to produce small batches of exceptionally fine spirits. From our micro-distillery in northeast Minneapolis, we hand craft each batch with the hopes of inspiring legendary cheer in those who drink it.
14
First Unitarian Meeting House of Madison
15
Alliant Energy Center
Our premier downtown multi-venue complex features four unique and versatile venues: Veterans Memorial Coliseum, Exhibition Hall, the New Holland Pavilions, and Willow Island. A top choice for expositions, conventions, meetings, concerts, sporting events, ag events, and much more, the Alliant Energy Center complex is a one-stop-shop for all your events. Ample parking, mouthwatering catering, dedicated staff, and a full range of rental equipment & high speed internet make AEC an event planners delight!
16
Anderson Japanese Gardens
Anderson Japanese Gardens is proud of its longstanding reputation as one of the highest quality Japanese gardens in North America. Our passion, however, is how the Garden positively impacts individuals and the communities where they live. We are committed to presenting first-class programs, events, and opportunities that bring people together in this uplifting natural setting.
17
Klehm Arboretum & Botanic Garden
This year-round garden, which started as a commercial nursery, includes 155 acres of trees and 300 woody plant species mapped and labeled. The gardens include: a Rhododendron and Azalea dell, Hosta Garden, Nancy Olsen's Children's Garden, Fountain Garden, Demonstration Garden, Peony Garden, Grasses Garden,Woodland Wildflower Garden and Plant-a-Row garden. There are several signature events hosted each year also. Botanica luncheon,Garden Fair, Plant Sale, Woodsong Concert Series, Autumn in the Arboretum and Twilight in the Garden are all popular annual events.
18
Arista Spa & Salon
Arista Spa & Salon in Naperville, Illinois has been artfully designed with attention to the finest details to soothe the body and enrich the soul. In this special place we bring together ancient Mediterranean healing with modern innovation, cherished rituals for cleansing and wellness with the best science has to offer your skin, hair and body. All in inspiring surroundings with a staff that is both nurturing and world class. The Arista Spa & Salon and its services have been crafted to meet the needs of both men and women. You may also enjoy our inspiring couples' room, allowing you to experience complete relaxation with someone special.
19
Wrigley Field
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
20
Boystown
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
21
The Chopping Block
The Chopping Block, Chicago's premiere recreational cooking school and gourmet retail store, offers demonstration and hands-on cooking classes, as well as wine classes, private cooking parties and corporate team building events. Classes at Lincoln Square cover subjects from cooking basics to intensive Boot Camps as well as seasonal, date nights, healthy and kids classes. We have a food-friendly wine selection so students can select beverages to pair with the menu of their class. Sorry, BYOB is not allowed.
22
Michigan Avenue Bridge
The view from the bridge is one of the best vistas the city has to offer.
23
Allen County War Memorial Coliseum
24
Lakeside Park & Rose Garden
25
Sprucewood Shores Estate Winery
The Sprucewood Family warmly welcomes you to sample handcrafted 100% Ontario VQA wines at Ontario's only beachfront destination vineyard, winery and tasting room. We are situated on 45 Acres with access to gardens, a sandy beach, and picnic tables. Enjoy a glass of wine with a picnic basket and explore our grounds year round. Tasting room open 7 days a week 11am - 5pm (we occasionally close early due to special events. Please check our social media for daily updates @sprucewoodshores)
26
Rock & Roll Hall of Fame
Headquartered in a boldly designed building on Lake Erie's shore, The Rock and Roll Hall of Fame is a 150,000-square-foot museum featuring ever-changing exhibits documenting the history of rock and roll, from Elvis to our days. You’ll see hundreds of original artifacts, from Jimi Hendrix outfits to The Beatles’ handwritten lyrics. Experience the excitement of a Rock Hall induction night at the Power of Rock Experience or have your very own jam session at the Garage. You can also watch a concert while you're here, so check out the Rock Hall’s schedule and plan ahead. – Tripadvisor
27
Federal Reserve Bank of Cleveland: Education and Learning Center
Ever wonder how money works or what the Federal Reserve Bank of Cleveland does as part of the central bank of the US? Visit our Education and Learning Center featuring more than 25 fun, hands-on exhibits that answer these questions and more! We have interactive games, visual exhibits, creative stations, and illuminating films that explain everything about money you can think of, from how we use it, to why it looks the way it looks. Come see our historic lobby, take pictures with our money tree, trade coconuts on Barter Island, identify counterfeit bills, and even make your own money! All this in the heart of Cleveland, just steps away from downtown attractions. Admission is free and photos are welcome.
28
GE Chandelier
29
Lock 3
30
Point State Park
Serving as a key strategic spot during the French and Indian War, this National Historic Landmark and park offer stunning views of the city and a variety of outdoor recreation.
31
Cathedral of Learning
Customize this Trip
OVERVIEW
Anchorage to Chesapeake
1
Start:Fort Ward Museum & Historic Site
Alexandria, Virginia·
4.0
(71) review
4301 W Braddock Rd, Alexandria, VA 22304-1007
2
Start:St. Paul's Episcopal Church
Richmond, Virginia·
4.5
(94) review
815 E Grace St, Richmond, VA 23219-3409
3
Start:Rockwood Park
Richmond, Virginia·
5.0
(9) review
3401 Courthouse Rd, Richmond, VA 23236-1438
4
Start:The Mariners' Museum and Park
Newport News, Virginia·
5.0
(959) review
Curate your Mariners’ Experience! From inspiring stories of mariners who risked it all for freedom to true tales of man conquering the wild seas, our indoor galleries will spark curiosity, wonder, and an appreciation for our shared maritime heritage. Explore over 90,000 square feet of gallery space and discover your connection to our shared maritime heritage. Admission to the Museum is only $1 per person. Add some outdoor adventure to your day in our 550-acre Park which offers visitors a quiet and serene place to walk, hike or run amongst rolling woodlands. Our Park features the award-winning five-mile Noland Trail that surrounds the 167-acre Mariners’ Lake. The Park is free and open to the public.
5
Start:O'Connor Brewing Co.
Norfolk, Virginia·
4.5
(97) review
The brewery is located at 211 W. 24th Street in the new Railroad district of Norfolk, situated next to the historic Ghent neighborshood and just a mile or two from Downtown. The Tasting Room and Production facility share a 35,000 sq. foot mid-century modern historic building. Free parking is available in their private lot or street parking is free along 24th and 23rd street. O’Connor beer drinkers come from all walks of life, but what brings them together is a love of the small, simple joys in life. The pleasure of being outdoors, relaxing on the beach with friends, having dinner with family after a day of hard work, and of course, enjoying a fresh, flavorful beer. Customers appreciate the O’Connor brand for its approachability and authenticity. They value its independent spirit, that it remains family owned and operated, and its support of the local community. And their loyalty has established it as a mainstay brand with 10 years of sustained success.
6
Start:Girdwood Brewing Company
Girdwood, Anchorage, Alaska·
4.5
(97) review
Enjoy local brews and epic views of the Chugach mountains at Girdwood Brewing Company. We have a beautiful timber framed taproom adorned with local art and ski relics. For those who prefer the outdoors, there’s an awesome beer garden with fire pits and plenty of seating. We offer up four core beers and a series of rotating taps. Root beer, cold brew coffee, and kombucha are available for those looking for an alcohol free beverage. Tasters and 12 ounce pours are available to drink in the taproom. If you are looking for beer to go, we fill growlers, sell 5 gallon kegs, and have 4-packs of 16 ounce cans with labels designed by Alaskan artists (for sale in the taproom only). Food trucks are on-site every day, and we have cool merchandise for you to take home. Girdwood Brewing Company is truly rooted in our community. We donate to a number of nonprofits and outdoor adventure organizations. Our brewery also provides year round employment to over a dozen locals.
7
Start:Flattop Mountain Trail
Anchorage, Alaska·
4.5
(949) review
13229 Glen Alps Rd, Anchorage, AK 99516-6967
8
Start:Indian Valley Mine, National Historic Site
Indian, Anchorage, Alaska·
4.5
(95) review
The main cabin, which contains the gift shop, and the assay building at Indian Valley Mine has some of the oldest structures built on the Turnagain Arm, and are listed as a National Historic Site. Indian Valley Mine offers visitors the opportunity to learn gold panning and browse through two historic cabins built in the early 1900's a small museum and gift shop, or simply sit back on one of our benches and take in the panoramic view of the Turnagain Arm.
9
Start:Planet Walk
Anchorage, Alaska·
3.5
(8) review
5th & G Street Kincaid Park, Anchorage, AK
10
Start:Four Seasons Trans Group
Anchorage, Alaska·
5.0
(98) review
We provide shuttle services within Anchorage, Seward, Talkeetna, Whittier, Palmer, Wasilla, and Girdwood.
11
Start:Acme Comedy Co.
Minneapolis, Minnesota·
3.5
(93) review
708 N 1st St, Minneapolis, MN 55401-1133
12
Start:Indeed Brewing Company
Minneapolis, Minnesota·
4.5
(94) review
711 15th Ave NE, Minneapolis, MN 55413-1738
13
Start:Norseman Distillery
Minneapolis, Minnesota·
5.0
(98) review
Norseman Distillery, the first micro-distillery in Minneapolis, was founded with principles of using the very best local ingredients to produce small batches of exceptionally fine spirits. From our micro-distillery in northeast Minneapolis, we hand craft each batch with the hopes of inspiring legendary cheer in those who drink it.
14
Start:First Unitarian Meeting House of Madison
Madison, Wisconsin·
4.5
(96) review
900 University Bay Dr, Madison, WI 53705-2298
15
Start:Alliant Energy Center
Madison, Wisconsin·
4.0
(99) review
Our premier downtown multi-venue complex features four unique and versatile venues: Veterans Memorial Coliseum, Exhibition Hall, the New Holland Pavilions, and Willow Island. A top choice for expositions, conventions, meetings, concerts, sporting events, ag events, and much more, the Alliant Energy Center complex is a one-stop-shop for all your events. Ample parking, mouthwatering catering, dedicated staff, and a full range of rental equipment & high speed internet make AEC an event planners delight!
16
Start:Anderson Japanese Gardens
Rockford, Illinois·
4.5
(863) review
Anderson Japanese Gardens is proud of its longstanding reputation as one of the highest quality Japanese gardens in North America. Our passion, however, is how the Garden positively impacts individuals and the communities where they live. We are committed to presenting first-class programs, events, and opportunities that bring people together in this uplifting natural setting.
17
Start:Klehm Arboretum & Botanic Garden
Rockford, Illinois·
4.5
(83) review
This year-round garden, which started as a commercial nursery, includes 155 acres of trees and 300 woody plant species mapped and labeled. The gardens include: a Rhododendron and Azalea dell, Hosta Garden, Nancy Olsen's Children's Garden, Fountain Garden, Demonstration Garden, Peony Garden, Grasses Garden,Woodland Wildflower Garden and Plant-a-Row garden. There are several signature events hosted each year also. Botanica luncheon,Garden Fair, Plant Sale, Woodsong Concert Series, Autumn in the Arboretum and Twilight in the Garden are all popular annual events.
18
Start:Arista Spa & Salon
Naperville, DuPage County, Illinois·
4.0
(9) review
Arista Spa & Salon in Naperville, Illinois has been artfully designed with attention to the finest details to soothe the body and enrich the soul. In this special place we bring together ancient Mediterranean healing with modern innovation, cherished rituals for cleansing and wellness with the best science has to offer your skin, hair and body. All in inspiring surroundings with a staff that is both nurturing and world class. The Arista Spa & Salon and its services have been crafted to meet the needs of both men and women. You may also enjoy our inspiring couples' room, allowing you to experience complete relaxation with someone special.
19
Start:Wrigley Field
Chicago, Illinois·
4.5
(9953) review
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
20
Start:Boystown
Chicago, Illinois·
4.5
(98) review
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
21
Start:The Chopping Block
Chicago, Illinois·
4.5
(98) review
The Chopping Block, Chicago's premiere recreational cooking school and gourmet retail store, offers demonstration and hands-on cooking classes, as well as wine classes, private cooking parties and corporate team building events. Classes at Lincoln Square cover subjects from cooking basics to intensive Boot Camps as well as seasonal, date nights, healthy and kids classes. We have a food-friendly wine selection so students can select beverages to pair with the menu of their class. Sorry, BYOB is not allowed.
22
Start:Michigan Avenue Bridge
Chicago, Illinois·
4.5
(985) review
The view from the bridge is one of the best vistas the city has to offer.
23
Start:Allen County War Memorial Coliseum
Fort Wayne, Indiana·
4.0
(99) review
4000 Parnell Ave, Fort Wayne, IN 46805-1414
24
Start:Lakeside Park & Rose Garden
Fort Wayne, Indiana·
4.5
(96) review
1401 Lake Ave, Fort Wayne, IN 46805
25
Start:Sprucewood Shores Estate Winery
Harrow, Essex, Ontario·
4.5
(97) review
The Sprucewood Family warmly welcomes you to sample handcrafted 100% Ontario VQA wines at Ontario's only beachfront destination vineyard, winery and tasting room. We are situated on 45 Acres with access to gardens, a sandy beach, and picnic tables. Enjoy a glass of wine with a picnic basket and explore our grounds year round. Tasting room open 7 days a week 11am - 5pm (we occasionally close early due to special events. Please check our social media for daily updates @sprucewoodshores)
26
Start:Rock & Roll Hall of Fame
Cleveland, Ohio·
4.5
(9964) review
Headquartered in a boldly designed building on Lake Erie's shore, The Rock and Roll Hall of Fame is a 150,000-square-foot museum featuring ever-changing exhibits documenting the history of rock and roll, from Elvis to our days. You’ll see hundreds of original artifacts, from Jimi Hendrix outfits to The Beatles’ handwritten lyrics. Experience the excitement of a Rock Hall induction night at the Power of Rock Experience or have your very own jam session at the Garage. You can also watch a concert while you're here, so check out the Rock Hall’s schedule and plan ahead. – Tripadvisor
27
Start:Federal Reserve Bank of Cleveland: Education and Learning Center
Cleveland, Ohio·
4.5
(95) review
Ever wonder how money works or what the Federal Reserve Bank of Cleveland does as part of the central bank of the US? Visit our Education and Learning Center featuring more than 25 fun, hands-on exhibits that answer these questions and more! We have interactive games, visual exhibits, creative stations, and illuminating films that explain everything about money you can think of, from how we use it, to why it looks the way it looks. Come see our historic lobby, take pictures with our money tree, trade coconuts on Barter Island, identify counterfeit bills, and even make your own money! All this in the heart of Cleveland, just steps away from downtown attractions. Admission is free and photos are welcome.
28
Start:GE Chandelier
Cleveland, Ohio·
4.5
(9) review
E 14th St, Cleveland, OH 44115
29
Start:Lock 3
Akron, Ohio·
4.5
(98) review
200 S Main St, Akron, OH 44308-1315
30
Start:Point State Park
Pittsburgh, Pennsylvania·
4.5
(951) review
Serving as a key strategic spot during the French and Indian War, this National Historic Landmark and park offer stunning views of the city and a variety of outdoor recreation.
31
Start:Cathedral of Learning
Pittsburgh, Pennsylvania·
4.5
(979) review
4200 5th Ave., Pittsburgh, PA 15260
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FAQ
Frequently Asked Questions
What's the driving distance between Anchorage and Chesapeake?
The distance is 4,461 miles
What's the travel time between Anchorage and Chesapeake?
The driving time can vary depending on traffic conditions, but it is typically 88h 19m mins in normal traffic
What are some of the best cities to visit between Anchorage and Chesapeake?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Chesapeake?
There are plenty! Here are some stops you shouldn’t miss on your way to Chesapeake
What’s the weather like in Chesapeake?
The weather in Chesapeake is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Chesapeake in January
Weather in Chesapeake in February
Weather in Chesapeake in March
Weather in Chesapeake in April
Weather in Chesapeake in May
Weather in Chesapeake in June
Weather in Chesapeake in July
Weather in Chesapeake in August
Weather in Chesapeake in September
Weather in Chesapeake in October
Weather in Chesapeake in November
Weather in Chesapeake in December
Interested in a detailed plan for your time in Chesapeake?
Plan your dream Chesapeake trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Chesapeake
A 2-day itinerary in Chesapeake
A 3-day itinerary in Chesapeake
A 4-day itinerary in Chesapeake
A 5-day itinerary in Chesapeake
A 6-day itinerary in Chesapeake
Where else can I travel to if I'm starting my trip in Anchorage?
We have a lot of great trip options for Anchorage! See the links below for all the itineraries we created for you