The Best Romantic Road Trips in the USA

Giulia Nigrini
Giulia Nigrini
Vehicle Service Contract Specialist, Traveler, Car Enthusiast
January 26, 2022
min. read
a garden scene full of green plants that has a romantic setting

Soon the most romantic of holidays will be here. A time when we celebrate those dear to our hearts. A great way to spend a wonderful time together is going on a scenic and romantic road trip through the many amazing states in the USA. There are breathtaking landscapes, a wealth of culture, and incredible culinary experiences waiting to be explored. Read on as we explore the best romantic road trips in the USA.

01 Chicago to Madison County

There is no doubt that Chicago has a certain beauty about it. Start your trip here to enjoy Lake Michigan and the unique food. Fun dishes like the deep dish pizza, the Jibarito sandwich, the Italian beef sandwich, or the Chicago style hot dog. Plus you have a range of romantic hotels to choose from. Making it one of the best romantic road trip starting cities.

Enjoy the Chicago Botanic Garden

A beautiful garden expresses such a connected sensation to romance. The magic that nature has to offer can bring about calmness and make you feel more relaxed than you might imagine. The Chicago Botanic Garden offers an incredible 380 acres of plants you and your partner can simply enjoy. For a particularly romantic visit you can go for the The Orchid Show: Untamed taking place from 12 February to 27 March 2022.

Sail on Lake Michigan

Lake Michigan is one of the great lakes and allows you to take in the famous skyline of Chicago. After a wonderful time spent taking in the romantic flowers, we would suggest sailing on Lake Michigan. Two favorites are the 114-foot Manitou and the 148-foot tall ship Windy of Chicago that sail in the evenings for a wonderful sunset.

Dine at NoMI

To end off your romantic day in Chicago we would suggest getting a reservation at NoMI. At NoMI you will be able to view the Water Tower and Lake Michigan while you indulge in a luxurious dinner. The menu showcases tasty cocktails and a French inspired cuisine that will delight you and your partner.

Off to Madison County

Now you are well rested and certainly relaxed after your romantic day in Chicago. It is time to hit the road for Madison county. We would suggest driving to Winterset where there are a number of lowkey romantic getaways where you and your partner can go to just wind down.  

Covered Bridges Winery

Madison county is well-known for its covered bridges that have been featured in a number of films. Going and visiting some of these bridges will give you and your partner the opportunity to take amazing photos that will be ones for the wall. One of the best stops here will be a visit at the Covered Bridges Winery where you will love the wine, food, and entertainment offered at their events. Such as the Valentine’s dinner on 12 February. This is a great place to end your journey and spend a pleasant evening together.

02 Route 100, Vermont

Vermont has much history and culture to experience. Route 100, Vermont, is known as the Skier’s Highway as it connects to many popular skiing destinations. Other activities include hiking, biking, riding, and golf.

Okemo Mountain Resort

If adventure is your thing then this is perfect for you. The Okemo Mountain Resort has all year round activities that include the 121 hiking trails in the extensive mountainous region. The Jackson Gore Peak, Solitude Peak, South Face, Glades Peak and South Ride are all under the Okemo Mountain Resort, which makes this snowy paradise a great place for mountain biking. Something that can be romantic and peaceful. Enjoy a night here to take in the splendid atmosphere.

Green Mountain Sugar House in Ludlow

Now that you have taken a romantic adventure in the mountains, a delicious sweet stop off of Route 100 will sweeten the whole experience. The Green Mountain Sugar House was built in 1967 by a darling couple that has made award winning maple syrup. Here you can enjoy the lovely scenery and wholesome food for a romantic breakfast on your journey.

The Rochester Cafe & Country Store

After your breakfast hit the road to the Rochester Cafe & Country Store. The drive is about an hour but there are plenty of places to stop by and explore. Take your time on the journey. When you get to the cafe you and your partner will love the country shop filled with local products such as jewelry, jams, soaps, toys, and clothing. Here you can buy a special memento of your trip and have a really tasty lunch before you complete the rest of your road trip.

Cold Hollow Cider Mill in Waterbury Center

The last leg of this journey will take you about 2 hours and 30 minutes with a few stops at some of the fascinating towns along the way. Drive to Moose Meadow Lodge & Treehouse in Waterbury to check in for an glamorous cabin evening before going to Cold Hollow Cider Mill for the cider and all the sweet treats. Make sure to book a room in advance for you and your partner, especially if you are going between May and October when the treehouse is available for use.

03 New York City through Connecticut

For a more low key drive that is not such a distance, we would recommend taking a trip from New York through Connecticut. You may be surprised by how much is offered in this relatively small area. We find this route to be one of the best romantic road trips in the USA that is great all year round as well.

Katonah – Marian Yarrow Green Trail

Start your road trip by driving up to Katonah where you will be able to see early Victorian houses and have a delightful breakfast before going to Marian Yarrow Green Trail for a nature immersed loop hike. The hike is not very long and will give you an ideal opportunity to take some desirable couples photos.

Croton Falls

After your romantic hike through the forest and meadows take the road to Croton Falls. The area is filled with orchards and other fabulous farms. We would recommend checking out Outhouse Orchards where you can book to go apple picking or adventure through the corn maize. They also have a farm shop where you can buy some great local produce. For lunch we would definitely recommend going to Purdy’s Farmer & The Fish for world class dining. The atmosphere and the food will leave you totally satisfied during your romantic road trip.

Ethan Allen Hotel in Danbury

From Croton Falls take the road to Ethan Allen Hotel in Danbury to spend your first romantic evening with your partner. The hotel has beautiful architecture and gardens. Book the Romance Package beforehand so that when you arrive you can wind down together with a bottle of prosecco. In the morning you both will then have a grand breakfast.

Glebe House Museum & The Gertrude Jekyll Garden

For a slightly unusual turn, take the road to Woodbury after you have got yourselves ready to continue your road trip. Here you will find the Glebe House Museum & The Gertrude Jekyll Garden. The house was built in 1740 and is one of the oldest historical homes in the USA. Later the house was accompanied by a beautiful garden designed by Gertrude Jekyllin 1926. This is a very scenic and picturesque visit that will simply add a sense of wonder to your road trip.

Winvian Farm

What better way to end your road trip than a stay in a luxury cottage on a romantic and historic farm? The Winvian farm offers a variety of themed cottages that are all nestled away in the forest and meadows. The area is so peaceful it makes anyone feel tranquil. Plus they have a number of activities like spirit tasting and bonfire s’mores. This is the ideal spot to spend one last night together, just you and your partner.

Plan your Road Trip

No matter where you find yourself taking a road trip, be sure to stop at all the small towns as you never know what you might find hidden away. Gems are special because they are hard to find and bring a smile to your face.

Before you go, be sure to plan your road trip well in advance. Checking that all necessary items are packed and doing a car inspection are just two important checks to do before driving off. To include in your list of important items would be an extended car warranty or vehicle service contract. This will ensure that you will have protection in the event of a mechanical breakdown. With an extended warranty plan you can be sure that you will have the repairs covered for critical mechanical damage. On top of this you get great added benefits that include roadside assistance, trip-interruption services, and gas delivery services should you get stuck on the side of the road.

What does an Extended Car Warranty Cover?

Third-party aftermarket auto warranty providers offer powertrain plans, powertrain plus, and bumper-to-bumper plans that cover the most critical components of your vehicle. Powertrain plans sit on the most basic tier of warranty options and ensure that all of the parts within your car’s powertrain will be covered. These parts include:

Powertrain plus warranties cover the same basic critical components as the powertrain warranty but also include a few adjacent systems which includes the following:

Bumper-to-bumper warranties cover the same parts as the powertrain plan but then include electrical components, the fuel system, A/C, and cooling systems and are more comprehensively covered than the powertrain plus warranties. Sometimes referred to as an exclusionary warranty due to having fewer parts not covered than those covered. Components typically excluded from bumper-to-bumper warranties are very few and include:

Many of the plans the providers on Chaiz offer wonderful perks to go with your aftermarket auto warranty/vehicle service contract purchase. Find out more on our blog or search for your specific vehicle on the Chaiz search tool.

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