Outdoor Activities

There are many reasons to get outside this Fall. Celebrate fall by attending a Halloween parade. Support a cause that gives back to the community by attending a walk or half marathon. Take in the beauty of nature by checking out a local park or hiking trail. 


Wilton Pumpkin Parade

Saturday, October 27th 12:00pm

Great day for kids to show off their costumes and trick or treat in Wilton.


New Canaan Halloween Parade

October 28th, 12:00pm

Ghosts, goblins, fairy princesses, superheroes, children of all ages and dogs are invited to participate. The fun starts at the park Street Parking Lot at Noon. Stop by for a goody bag, live music, and entertainment for kids.


Stamford Downtown Parade Spectacular

November 18th 12 Noon

Giant Helium Balloon Parade Spectacular presented by Stamford Advocate/Hearst Connecticut Media Group. One of the largest helium balloon parades in the country, featuring everyone’s favorite characters, marching bands and floats!


Halloween Pet Parade- Pequot

October 27th 2-3:30pm

Bring your pets in costume to march in the townwide Halloween Pet Parade held by the Pequot Library. Enjoy old fashioned Halloween games on the Library’s Great Lawn. As well as free refreshments and entertainment by Mary Ann Hall’s Music for Children.



SoNo Half Marathon- Wilton, CT

October 20th 9am-12:15pm

Bring the whole family for a day of fun and fitness! There will be music along the half marathon and 5k courses as well at a post race party featuring food and refreshments, music, awards ceremony and more.


Walk with Jake K9 Fundraiser- Fairfield, CT

October 21st 11:00am, walk starts at 12pm

Walk with Fairfield Police K9 Jake in support of Fairfield Police Department K9 Unit. The dog walk will be held on Jennings Beach to raise awareness of PTSD. There will also be a Halloween costume contest, a police K9 demonstration, some great giveaways, pizza and music!


Out of the Darkness Walk- Westport, CT

October 27th 11am-2pm

Join the effort to raise awareness and funds for the American Foundation for Suicide Prevention. The Out of the Darkness Westport Walk will loop around Sherwood Island with serene views of the Sound and the 9-11 Memorial, suitable for strollers and dogs as well.


Walktober- Danielson, CT

Saturday, September 22- Sunday, November 4

This year is the 28th Annual Walktober in the Last Green Valley National Heritage Corridor. Walktober is the best way to celebrate all the beauty, historic treasures and working farms of the 35 towns of eastern Connecticut and south-central Massachusetts. Join Walktober 2018 with more than 250 walks, hikes, historic tales, paddles, bike rides, farm visits, and more.



Nature Conservancy- Devil’s Den Preserve- Weston, CT

Monday-Sunday: Sunrise to Sunset

Devil’s Den is Connecticut Chapter’s largest continuous preserve ideal for hiking and bird watching. The preserve has a twenty-mile trail system with a patchland of woodlands, wetlands and rock ledges.


Saugatuck Trail-Weston, Redding

The Saugatuck Trail is located within the 15,000 acre Centennial Watershed State Forest and parralels the Saugatuck Reservoir. The trail offers a variety of terrain and is 11.8 miles in total.


Tarrywile Park and Mansion- Danbury, CT

Monday-Sunday: 6am-6pm

From events in the Mansion to hiking in the park, Tarrywile has something to offer to everyone. The Park is home to 21 miles of hiking trails, 2 ponds, a lake and several picnic areas.


Veteran’s Park- Fairfield, CT

Veteran’s Park, located on Reef Road, is a nice clean park to bring kids to play or take a walk through. This park has volleyball poles, bocce courts, ball fields, and tennis courts.


Owen Fish- Fairfield, CT

Located on Stratfield Road, Owen Fish Park is a great park to have a picnic in or play a ball game.


Gould Manor- Fairfield, CT

Relax in nature at Gould Manor Park, located on Holland Hill Road.


Housatonic Railway Rails to Trails- Trumbull, CT

A beautiful “rail-trail” supported by the Rails-to-Trail Conservancy located in Trumbull.



2 Reviews
Must check out

So many great activities

November 2018

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Must check out!

So many great activities for the weekend

November 2018

Did you find this review helpful?


15 Oct 2018

By Eileen Sullivan