Top Spots For A Fall Marriage Proposal In Connecticut

Top Spots For A Fall Marriage Proposal In Connecticut
Planning a proposal and popping the question to your significant other can take time and effort. Don’t stress over the specifics as you start your planning. You are the expert in what makes the love of your life happy. The perfect proposal is defined differently for each person. Thus, the list below gives a variety of creative ways to pop the question in the fall. It is also proof that proposals can range from special purchases to make the day special, to more affordable options that mother nature has created.

Essex Steam Train & Riverboat 
1 Railroad Ave.
Essex, CT 06426
(860) 767-0103

All aboard the most memorable train ride of your life. Choose from two romantic options to ask the love of your life for their hand in marriage. The first option is the 2.5-hour fall foliage tour on the train and riverboat. Enjoy a ride through the Connecticut River Valley in vintage train coaches followed by a smooth ride on the Becky Thatcher Riverboat. Daytime time slots are available for this tour. The second option takes place in the evening, combining a romantic train ride with dinner. The Essex Clipper includes a 2.5-hour train ride with a four-course meal provided. Either option is a unique way to propose.

Gouveia Vineyards
1339 Whirlwind Hill Rd.
Wallingford, CT 06492
(203) 265-5526

Sitting on top of a hill in Wallingford, Gouveia Vineyard provides spectacular views year round. When you think of fall in New England, this vineyard is the perfect place to get foliage views. Plan for a sunny daytime proposal or catch the sunset later in the day. Gouveia allows visitors to bring their own food. Pack a meal or appetizers to eat indoors, outside on the lawn or at picnic tables, or escape to the more private area of the lake. You will be celebrating the thought of spending the rest of your lives together while sipping one of these delicious wines.

Sleeping Giant
200 Mt Carmel Ave.
Hamden, CT 06518
(203) 287-5658

For the athletic and outdoor type, plan a hike up one of the many trails at Sleeping Giant. Choose from the tower path, a direct trail that leads to the stone tower. At the top, you will have views of New Haven County and even Long Island Sound, or you can climb into the tower. You can also choose to hike a more private trail for seclusion from other hikers. Your significant other will fall in love with the breathtaking views, crisp air and surprise of a lifetime. Take a picture of the exact location of your proposal for special memories or to revisit from time to time.

Related:  Top Spots In Connecticut To Propose

River Quest Sunset Cruise
Little Meadow Rd.
Haddam, CT 06426
(860) 662-0577

Pop the question while cruising down the Connecticut River on a sunset cruise. River Quest has public or private sunset cruises on its 64-foot vessel. Reservations are required. Gather friends and family to join in on the surprise for a large group rate or rent a private charter. An alternative and more affordable option is the $30-per-person public cruise. Pack a picnic basket with your favorite foods and wine. As you cruise down the Connecticut River at sunset, you will have Kodak moment views of the foliage from the water.

Fairview Tree Farm
486 Walnut Tree Hill Rd.
Shelton, CT 06484
(203) 944-9090

This autumn, the Fairview Tree Farm is hosting hayrides. These hayrides are available for large groups or private rentals. Get cozy with a blanket along the 1.5-mile hayride. Travel to a pumpkin patch to find the perfect pumpkin to take home. Maybe the best pumpkin your significant other finds has a ring on it or is carved with the phrase “Will you marry me?”

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Kimberly Ord is a freelance writer and lifetime resident of Connecticut. Her work can be found at