5 Day New England Road Trip Itinerary

My friend Sheela was turning 50 and had only been to two New England states, Connecticut and Rhode Island. I planned a 5-Day New England Road Trip Itinerary to take her on starring a few of my favorite places in New England but staying southern enough to do in five days. We were given a zippy and fun bright red Mazda CX-50 to try, which added to the experience. I hope you can use our expertise to plan your next New England trip, maybe around a long weekend.

Because we are active women, we planned much of this trip around some of my favorite New England hikes. I also included the best of New England- the ocean, mountains, lighthouses, waterfalls, art, food, and covered bridges.

Day 1 Ogunquit, Maine

We wanted to start with a chill day by the water, so I picked one of my favorite New England seaside towns, Ogunquit. If you have extra time, Kennebunkport is not far away. My favorite thing in Ogunquit is walking the coastal Marginal Way path to Perkin’s Cove for a seafood feast. Read more about what to do in Ogunquit.

We stayed at the Juniper Hill Inn.

Day 2 Portland and Peaks Island, Maine

The food scene in Portland is fabulous; there are lots of lighthouses to explore, and you can take a quick ferry to a New England island, Peaks Island, which is easily explorable by bike. Read about what to do in Portland, Maine.

We stayed at the Portland Regency Hotel.

Day 3 The Kancamagus Highway, New Hampshire

The Kancamagus Highway travels through New Hampshire’s White Mountains and the towns of North Conway and Lincoln. Along the route are waterfalls, scenic overlooks, and hiking trails. Here are a few of my favorite Kanc hikes. On our trip, we hiked the Lower Falls and to Sabbaday Falls. My favorite winter hike is in Lincoln Woods.

Although I love both towns, it makes the most sense to stay in Lincoln so you aren’t doubling back. Check out this property in Lincoln, but stop in North Conway for breakfast at Peaches.

Day 4 The Lakes Region, New Hampshire

The town of Meredith sits on the banks of Lake Winnipesaukee. It is one of my favorite spots in New Hampshire. And just a few miles away is one of my favorite mountain hikes in New England, Mount Major. The peak of the hike provides views of Mount Washington and the surrounding lakes.

I have always wanted to stay at Mill Fall at the Lake.

Day 5 Woodstock and Quechee, Vermont

On our last day, we visited one of the most “New England” of the New England towns, Woodstock. It has a perfectly quaint downtown with a town green, lots of artists, and covered bridges over mountain rivers. The Quechee Gorge is an easy but beautiful hike. Woodstock is nestled in Vermont’s Green Mountains. Read on for things to do in Woodstock.

For a splurge, check out the gorgeously elegant Woodstock Inn.

Here is a map so that you can see a basic outline of the trip.

The Mazda CX-50

This 5-seater SUV was a very fun way to explore New England. It is zippy and has every feature I wanted, including crash avoidance and blind-side indicators. I also appreciated the lower gas mileage than my current SUV. It handled beautifully around our mountain roads and gave me all the power I hoped for.

With this 5-Day New England Itinerary, you will definitely be moving quickly. If you have more time, you can easily spend two days at any of these stops. Are you planning a trip to New England soon?

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