4 Colorful Fall Proposal Ideas That Will Leave Her Speechless

Author Sam Hussey
Date Feb 15, 2021

You know you want to pop the question before the holidays and with fall just around the corner, it's time to come up with a proposal plan that will sweep her off her feet. For all the outdoorsy/nature-loving Boston couples, let Massachusetts' natural beauty set the stage for this special moment.

There really is nothing like fall in New England. The cool crisp air, the return of our beloved Patriots, and of course, the breathtaking Autumn foliage. It doesn't matter how long you've lived in Boston, seeing the leaves transform to paint the trees a variety of reds, oranges, and yellows will always be sort of magical, which is why this is the perfect way to enhance your proposal!

From getting the ring, to proposing, to saying "I Do," and for every anniversary after, at Long's we take enormous pride in being there every step of the way to celebrate these life changing events with you. Here are our top four New England fall proposal ideas that we've seen over the years:

1) Picturesque Hike Proposal


Featuring: Clarke Pond on Coolidge Reservation

There really is no better season for hiking than fall in New England. The best part? No elaborate plan necessary. Just choose the hike, then let a fun day with your best friend and the picturesque autumn foliage set the stage for a breathtaking proposal she won't ever see coming.

Long's couple Kayla and Dan shared this special moment at one of their favorite hidden gem hiking locations in Manchester MA, Coolidge Reservation. With several different hiking trails that all lead to an amazing view on the "Ocean Lawn" overlooking Massachusetts Bay and the North Shore, there is really no wrong place to pop the question. Take a break on the forest trail surrounded by the colorful leaves, sit down by the pond, or leave the foliage in the background and take in the panoramic view of the sea on Coolidge's famous Ocean Cliffs like Dan did.

Coolidge Reservation is one of the many scenic New England hikes perfect for a fall proposal. We know it can be kind of overwhelming trying to narrow the endless trails, mountains, and reservations that pop up after Googling "best New England hikes (to propose)." To help you out a little - check out the top hikes for proposals in Massachusetts to find the best trail for the occasion.

2) New England Foliage Helicopter Tour Proposal



Featuring: A Long's Proposal Story: Lexi & Lance

This is the person you want to experience the rest of your life with, what better way to start than with something neither of you have done before? If you're looking for something out-of-the-box that will really blow her away (and don't mind the extra planning) a foliage helicopter tour is an amazing way to pop the question. Take in New England's natural beauty from above for an experience neither of you will ever forget.

In one of our favorite Long's proposal stories, our very own Marketing Director Lexi was completely surprised when Lance popped the question during their Seacoast Helicopter tour. As they were enjoying the stunning foliage and sea cost views, the pilot said they would have to make an emergency landing. Little did Lexi know Lance had it all planned out. Take note guys because this action-packed proposal is a great example of how you can make the proposal your own.

3) Colorful Boston Public Garden Proposal


Featuring: Boston Public Gardens

Simple and romantic - a Boston Public Gardens proposal is perfect for those of you who want to incorporate New England's colorful autumn foliage into your proposal without leaving the city. This is a great idea for the Boston men who would have trouble keeping the proposal plan a secret, because it's laid back and doesn't require an elaborate/complicated plan.

Whether you set a date or spontaneously decide to go for it on a nice night is up to you. All you have to do is ask your girl to go on a walk with you! This is a great location to propose if you think you might want to include your furry four-legged family member in the proposal. Here are a few of the ways you could include your dog in your fall proposal.

Another great idea for this location (that requires a little more stealth and planning) is to set up a picnic. Include fall themed foods like cider donuts from Union Square Donuts, apples, sparkling cider. Another great thing about Boston Public Gardens is you're just steps away from some of the best restaurants in the city, perfect for a post-proposal meal.

4) Intimate Apple Orchard Proposal


Featuring: Honey Pot Orchards, Photography by: Ashley O'Dell Photography

One of our favorite fall proposal ideas - propose at an apple orchard. If you're looking for something fun and romantic, one of Massachusetts' scenic apple orchards would make for a great proposal location. One of the 10 most beautiful places in Boston to propose, this seasonal activity has all the beauty of Boston Public Garden without all the hustle and bustle of the city. If you want this moment to be more private and intimate, Shelburne Farm or Honey Pot Orchards in Stow, MA could be the romantic spot you've been looking for. As ready as you are for this, it can be nerve-wracking when it comes time to finally get the words out. Take in the scenery under the guise of apple picking, and enjoy each others' company while you work up to the big question.

Another thing to note if you're thinking about hiring a photographer to capture special moment, the backdrop of a New England apple orchard in the fall will make for a picture-perfect proposal.

Have the perfect fall proposal planned but still searching for the perfect ring? Browse online or visit any of our five New England locations today!

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