Romantic Getaway Ideas for Fall Last Updated: November 2023

There are dozens of reasons why fall is considered one of the most romantic seasons of the year. Between the changing leaves, crisp air and roaring fireplaces—fall is the perfect time for a weekend away to unplug and reconnect with your significant other. To help you do just that, we’ve rounded up a selection of romantic fall getaway itineraries in Connecticut. This list of possibilities offers links to distinct, full itineraries. See which one appeals most, then just pack up, go and safely enjoy.

Small Town Getaways

Spend a romantic weekend in Wethersfield, an idyllic town that looks and feels as if you’re in a storybook. It is one of the oldest towns in Connecticut and encompasses all the charms of autumn in New England, including a historic B&B.

Escape to Essex and discover the beauty of Connecticut’s River Valley, known for its landscapes, majestic trees and gardens, fascinating architecture, and cultural and historical attractions, including a vintage steam train that offers four-course dinner rides.

Turn up the romance in Litchfield Hills, featuring some of the most brilliant foliage destinations in the state, such as Lake Waramaug. While exploring, you’ll find quaint towns, breathtaking views, natural wonders and spots to cozy up and relax.

Historic Charm

Go on a journey through Connecticut's revolutionary road. Visit homes, museums, parks and more, all of which contribute to Connecticut's part in the American Revolution.

From strolling through manicured gardens to spending the night in a charming cottage—experience country luxury with a Downton Abbey getaway in honor of the new movie of the hit TV series.

Walk hand-in-hand through a few of Connecticut’s picturesque bridges into the past. Or take in the breathtaking scenery from a birds-eye view during a hot air balloon ride (bring champagne to toast at the top).

Fall Foliage

Take the ultimate foliage tour of western Connecticut to discover one of the most well-known areas in the state for bright and brilliant foliage. Plan a picnic or go for a bike ride to take in the beauty. Leaves in this area typically peak in early to-mid October.

Head to the “Quiet Corner” of the state for the ultimate foliage tour of eastern Connecticut. Here you’ll travel on Route 169, a National Scenic Byway, that gets brightened up by foliage in early to-mid October.

Explore the lower Connecticut River Valley during this ultimate foliage tour of central Connecticut, with leaves beginning to peak in late October. Kayaking on the river and visiting a hidden waterfall are just a couple of the adventures you can expect to have during this getaway.

Autumn Routes and Trails

Sometimes the best leaf peeping views can be seen by car. The Route 7 getaway leads you to some of the most beautiful foliage spots in New England. Hop in the car and take your time following the route that National Geographic Traveler calls one of the most scenic driving destinations in the country.

From cityscape to countryside—follow this Merritt Parkway getaway to get a taste of both worlds. Art and culture lovers will be delighted by the gems this weekend escape has in store. Plus, you’ll pass through some of the area’s most charming farm towns.

Experience autumn along the Wine Trail by touring a few picturesque vineyards in Litchfield Hills. Pack a picnic with snacks to complement the unique flavors and stroll through the vines to take in the amazing vistas from every angle. 

Active Adventure, Relaxation & Gaming

If active adventures are more your speed, try biking the Quiet Corner. This getaway is filled with scenic backroads that lead to some of the area’s hidden gems, including quaint B&Bs, historic houses and romantic gardens.

Golf, pick apples, shop, dine and drink with this leisure getaway, which features a sampling of rural charms in eastern Connecticut.

Slow things down with a wellness getaway that features some amazing destinations to unwind. Book a couple’s massage, do outdoor yoga amongst the leaves or kayak the quiet waterways of a wildlife sanctuary to experience the full effects of this relaxing escape.

Stay at the Delamar and enjoy a luxury chauffeured experience in a classic car from Delamar hotels founder Charles Mallory's personal car collection. Ride in style through scenic routes and arrive at a stunning spot for a picnic, complete with a premium picnic basket, variety of wine, and chance to select from an autumn inspired menu, curated by Executive Chef Frederic Kieffer.

Make your escape extra exciting and plan a weekend at Connecticut's casinos. Enjoy gaming, dining, shopping, nightlife, spas, and more!